Ethyl Acetate → 3-Amino-2-(4-chlorobenzyl)aminopyridine

HRID 55499Notes

Reaction equation

HRID 55499 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8]2[C:13]([N+:14]([O-])=O)=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl.[BH4-].[Na+].C(OCC)(=O)C>CC(O)(C)C>[NH2:14][C:13]1[C:8]([NH:7][CH2:6][C:5]2[CH:17]=[CH:18][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 61436Stannous chloride dihydrateHCID 2800352N-[(4-chlorophenyl)methyl]-3-nitropyridin-2-amineHCID 4311764Sodium borohydride

Product 1

HCID 149530053-Amino-2-(4-chlorobenzyl)aminopyridine

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A procedure similar to that described in Preparation 42 was repeated, except that 5.00 g of 2-(4-chlorobenzyl) amino-3-nitropyridine (prepared as described in Preparation 52), 21.4 g of tin(II) chloride dihydrate, 0.36 g of sodium borohydride and 150 ml of a 9:1 by volume mixture of ethyl acetate and 2-methyl-2-propanol were used, to give the title compound as a crude product. This crude product was crystallized by trituration with a mixture of ethyl acetate and hexane, to give 3.55 g of the title compound, melting at 123°-125° C.

Workup

  1. customA procedure similar to that described in Preparation 42

Sources & evidence

ORD record
ord-d0af61da9a9b4a38be80efcaf4957e19
Source dataset
uspto-grants-1997_04
Patent number
US05624935

Reaction notes

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