Ammonium Chloride → HCID 90022767, compound

HRID 531462Notes

Reaction equation

HRID 531462 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]=2)=[C:4]([N+:21]([O-])=O)[CH:3]=1.[Cl-].[NH4+]>C1COCC1.O.[Zn]>[NH2:21][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=1[C:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 90030812HCID 90030812, compound

Product 1

HCID 90022767HCID 90022767, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Using similar reaction conditions as described in step ii of Intermediate-27, tert-butyl 4-(4-bromo-2-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate (450 mg, 1.17 mmol) was reduced using zinc dust (610 mg, 9.39 mmol) and ammonium chloride (1.0 g, 18.72 mmol) in THF/water 10/5 ml to afford 300 mg (72.4% yield) of the titled product after purification with (60/120 silica gel) column chromatography using 30% ethyl acetate in hexane as eluent. MS: m/z=295.1 (M-Boc+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-64321a4352554783b2c3745c25a77b47
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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