Acetic Acid → HCID 178509842, compound

HRID 2415071Notes

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

Participants

Reactant 3

HCID 176Acetic Acid

HCID 167023-Aminobenzonitrile

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

Product 1

HCID 178509842HCID 178509842, compoundYield 78%

Procedure

Prepared from the dimethylaminomethylene derivative (Procedure E) of 1,3-dihydro-2H-pyrrolo[3,2-f]quinolin-2-one (Procedure C) with 3-aminobenzonitrile according to Procedure G in acetic acid to give the title compound in 78% yield as the acetate salt. 1H NMR (DMSO-d6) δ: 1.88 (s, 3H); 7.39 (d, J=8.5 Hz, 1H); 7.45-7.6 (m, 3H); 7.78 (m, 2H); 8.20 (s, 1H); 8.75 (d, J=4 Hz, 1H); 8.8-8.9 (m, 2H); 11.0 (s, 1H); 11.8 (d, J=12 Hz, 1H); 11.95 (s, 1H). ES-MS: m/z 313 (M+H)+.

Sources & evidence

ORD record: ord-2267f41d170a4dc5a5c6bbfbf9eda1a6
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06818632B2

Reaction notes

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