Acetic Acid → HCID 178492231, compound

HRID 840910Notes

Reaction equation

[CH2:1]1[C:5]2=[C:6]3[C:11](=[CH:12][CH:13]=[C:4]2[NH:3][C:2]1=[O:14])[N:10]=[CH:9][CH:8]=[CH:7]3.[CH3:15][O:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1.[C:24](O)(=O)C>>[CH3:15][O:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21]/[CH:24]=[C:1]2\[C:2](=[O:14])[NH:3][C:4]3[C:5]\2=[C:6]2[C:11](=[CH:12][CH:13]=3)[N:10]=[CH:9][CH:8]=[CH:7]2)=[CH:19][CH:18]=1

Participants

Reactant 3

HCID 176Acetic Acid

HCID 7732P-Anisidine

HCID 219070851,3-Dihydro-pyrrolo[3,2-f]quinoline-2-one

Product 1

HCID 178492231HCID 178492231, compoundYield 54%

Procedure

Prepared from the dimethylaminomethylene derivative (Procedure E) of 1,3-dihydro-2H-pyrrolo[3,2-f]quinolin-2-one (Procedure C) with 4-methoxyaniline according to Procedure G in acetic acid to give the title compound in 54% yield as the acetate salt. 1H NMR (DMSO-d6) δ: 1.88 (s, 3H); 3.75 (s, 3H); 6.97 (d, J=8.9 Hz, 2H); 7.39 (d, J=8.7 Hz, 1H); 7.43-7.5 (m, 3H); 7.68 (d, J=8.5 Hz, 1H); 8.70 (d, J=4.0 Hz, 1H); 8.75-8.82 (m, 2H); 10.9 (s, 1H); 11.75 (d, J=12 Hz, 1H); 11.9 (s, 1H). ES−MS: m/z 318 (M+H)+.

Sources & evidence

ORD record: ord-a9a2cbec230041fb9aebd911fd2c17ca
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06369086B1

Reaction notes

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