P-Anisidine → HCID 68692783, compound

HRID 2236935Notes

Reaction equation

HRID 2236935 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[CH:13][N:14]([CH3:16])C)[C:7](=[O:12])[NH:8][CH2:9]2)=[CH:4][CH:3]=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23]C(N)=[CH:21][CH:20]=1>CN(C)C=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[CH:13][NH:14][C:16]3[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=3)[C:7](=[O:12])[NH:8][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 68695722HCID 68695722, compound

Product 1

HCID 68692783HCID 68692783, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

To a suspension of crude 7-bromo-4-dimethylaminomethylene-1,4-dihydro-2H-isoquinolin-3-one (400 mg, 1.43 mmol) in N,N-dimethylformamide (250 mL) is added 4-anisidine (193 mg, 1.57 mmol). The reaction mixture is shaken at 115° C. for 1.5 hours. The reaction mixture is filtered and the filtrate is purified by Prep. HPLC. The pure fractions were combined and concentrated to yield 114 mg of 7-Bromo-4-[(4-methoxy-phenylamino)-methylene]-1,4-dihydro-2H-isoquinolin-3-one.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is purified by Prep
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-72c4a7d097f04461b5b655decd53fa6b
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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