4-Aminobiphenyl → HCID 178518314, compound

HRID 2236592Notes

Reaction equation

HRID 2236592 reaction equation
CO[CH:3]=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[NH:6][C:5]1=[O:15].[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:19][CH:18]=1>CN(C)C=O>[C:20]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:19]=[CH:18][C:17]([NH:16]/[CH:3]=[C:4]2\[C:5](=[O:15])[NH:6][C:7](=[O:14])[C:8]3[C:13]\2=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 71024-AminobiphenylHCID 686923374-Methoxymethylene-4H-isoquinoline-1,3-dione

Product 1

HCID 178518314HCID 178518314, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 0.500 g (2.46 mmol) of 4-methoxymethylene-4H-isoquinoline-1,3-dione and 0.416 g (2.46 mmol) of 4-aminobiphenyl in 8 mL of N,N-dimethylformamide is heated at 105° C. under N2 for 1.5 h. The reaction is then chilled in ice and the solid product is collected. It is washed with cold N,N-dimethylformamide (DMF) and Et2O and dried in vacuo to give 0.295 g (35%) of yellow crystals: mp 261-262° C.; 1H NMR (DMSO-d6) δ 12.5 (d, 1H, J=9 Hz), 11.4 (s, 1H), 9.94 (d, 1H, J=9 Hz), 8.21 (d, 1H, J=6 Hz), 8.05 (d, 1H, J=6 Hz), 7.68 (m, 7H), 7.47 (m, 2H), 7.36 (m, 2H); HRMS (ESI) m/z calcd for C22H16N2O2 341.12846. found 341.12811 (M+H)+1; Analysis for C22H16N2O2; Calcd: C, 77.63; H, 4.74; N, 8.23. Found: C, 77.36; H, 4.66; N, 8.25.

Workup

  1. temperatureThe reaction is then chilled in ice
  2. customthe solid product is collected
  3. washIt is washed with cold N,N-dimethylformamide (DMF) and Et2O
  4. customdried in vacuo

Sources & evidence

ORD record
ord-e660661e433b424f9a46459db4301c62
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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