Water → HCID 178518255, compound

HRID 2236772Notes

Reaction equation

HRID 2236772 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[Br:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[NH:20][C:19](=[O:26])[C:18]2=[CH:27]OC.CCOC(C)=O.O>CN(C)C=O>[Br:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[NH:20][C:19](=[O:26])[C:18]2=[CH:27][NH:13][C:10]1[CH:11]=[CH:12][C:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 15126544-(Pyridin-4-yl)anilineHCID 686927644-methoxymethylene-6-bromo-4H-isoquinoline-1,3-dione

Product 1

HCID 178518255HCID 178518255, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Pyridin-4-yl-phenylamine (130 mg, 0.76 mmol) and 6-bromo-4-methoxymethylene-4H-isoquinoline-1,3-dione (200 mg, 0.71 mmol) is heated in N,N-dimethylformamide (10 mL) at 100° C. for 2 h. EtOAc (100 mL) and H2O (20 mL) is then added. The EtOAc layer is washed with H2O (3×20 mL) and brine (15 mL) and dried over MgSO4. After removal of EtOAc, the precipitate is collected and washed with MeOH and Et2O and dried to provide the title compound (230 mg, 77%). 1H NMR (300 MHz, DMSO) δ 12.59 (1H, d, J=12.9 Hz), 11.50 (1H, s), 9.0 (1H, d, J=12.6 Hz), 8.53-8.64 (3H, m), 7.43-7.95 (8H, m). MS (ESI) m/z 420.0, 422.0 (M+H)+1; Anal. Cacl. for C21H14BrN3O2: C, 60.02; H, 3.36; N, 10.00. Found: C, 59.4; H, 3.26; N, 9.34.

Workup

  1. washThe EtOAc layer is washed with H2O (3×20 mL) and brine (15 mL)
  2. dry with materialdried over MgSO4
  3. customAfter removal of EtOAc
  4. customthe precipitate is collected
  5. washwashed with MeOH and Et2O
  6. customdried

Sources & evidence

ORD record
ord-7ef225cb74c04a0fa6fdddd143b2b1a9
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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