Water → Methyl 2-(5-amino-1-oxoisoquinolin-2(1H)-yl)-2-(4-chlorophenyl)acetate

HRID 1161251Notes

Reaction equation

HRID 1161251 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[N+:23]([O-])=O)[C:14]2=[O:26])[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[Cl-].[NH4+].O>[Fe].ClCCl>[NH2:23][C:19]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:20]=1[CH:21]=[CH:22][N:13]([CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C:9]([O:11][CH3:12])=[O:10])[C:14]2=[O:26]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 58973969Methyl 2-(4-chlorophenyl)-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)acetate

Product 1

HCID 58973946Methyl 2-(5-amino-1-oxoisoquinolin-2(1H)-yl)-2-(4-chlorophenyl)acetate

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A round bottom flask was charged with methyl 2-(4-chlorophenyl)-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)acetate (4.2 g, 0.011 mol) ethanol (60 mL, 1 mol) and ammonium chloride (6 g, 0.1 mol) in water (60 mL, 3 mol) was added and the reaction heated at 80° C. and iron (2 g, 0.04 mol) was added in four portions 5 minutes apart. The reaction was heated for another 1 h at that temperature and cooled to room temperature and poured into 200 ml dichloromethane and extracted. The solvent was removed to obtain the product as a light brown solid. MS m/z=343.0 (M+H).

Workup

  1. additionwas added
  2. temperatureThe reaction was heated for another 1 h at that temperature
  3. temperaturecooled to room temperature
  4. extractionextracted
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-eea26390a0484865a5608c8b63455ad8
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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