amine syn 2

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1. H 3 C C O Cl AlCl 3 O HNO 3 H 2 SO 4 O NO 2 1. 2. H 3 O + CH 3 MgBr NO 2 OH H 2 SO 4 , ! NO 2 H 2 , Pd NH 2 N 2 + KCN CuCN CN NaNO 2 HCl 2. NaNO 2 HCl CO, HCl CuCl, AlCl 3 H O HNO 3 H 2 SO 4 H O NO 2 H 2 , Pd NH 2 N 2 + NaI I 3. HNO 3 H 2 SO 4 NO 2 Br 2 FeBr 3 NO 2 Br SnCl 2 HCl NH 2 Br N 2 + Br Br Br HBr CuBr NaNO 2 HCl
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4. excess AlCl 3 CH 3 Cl HNO 3 H 2 SO 4 separate NO 2 SnCl 2 HCl NH 2 N 2 + H 3 O + OH NaNO 2 HCl 5. HNO 3 H 2 SO 4 NO 2 Br 2 FeBr 3 NO 2 Br SnCl 2 HCl NH 2 Br N 2 + Br KCN CuCN CN Br H 3 O + , ! COOH Br NaNO 2 HCl 6. H 3 O + CO, HCl CuCl, AlCl 3 H O HNO 3 H 2 SO 4 H O NO 2 H 2 , Pd NH 2 N 2 + OH NaNO 2 HCl
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7. H 3 C C O Cl AlCl 3 O O Br Br 2 FeBr 3 H 2 , Pd Br HNO 3 H 2 SO 4 Br NO 2 sep 1. LAH, ether 2. H 2 O Br NH 2 Br N 2 + H 3 O + Br OH NaNO 2 HCl 8. excess AlCl 3 CH 3 Cl HNO 3 H 2 SO 4 separate NO 2 SnCl 2 HCl NH 2 N 2 + KCN CuCN CN H 3 O + , ! COOH NaNO 2 HCl
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9. HNO 3 H 2 SO 4 NO 2 Cl 2 FeCl 3 NO 2 Cl 1. LAH, ether 2. H 2 O NH 2 Cl Ac 2 O, pyr HN Cl O Br 2 FeBr 3 HN Cl O Br separate H 3 O + , ! NH 2 Cl Br KCN CuCN CN Cl Br 1. LAH, ether 2. H 2 O CH
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