alpha-Cyano-beta-(2-Nitro-4,5-Dimethoxyphenyl)Acrylamide → 2-Amino-6,7-dimethoxyquinoline-3-carboxamide

HRID 1283154

Reaction equation

[C:1]([C:3](=[CH:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[CH:10][C:9]=1[N+:18]([O-])=O)[C:4]([NH2:6])=[O:5])#[N:2]>[Fe].C(O)(=O)C.CN(C)C=O>[CH3:15][O:14][C:12]1[CH:13]=[C:8]2[C:9](=[CH:10][C:11]=1[O:16][CH3:17])[N:18]=[C:1]([NH2:2])[C:3]([C:4]([NH2:6])=[O:5])=[CH:7]2

Participants

Conditions

Temperature: 90 °C

Procedure

Iron powder (65.2 g., 1.22 moles) is added over a period of one-half hour to a slurry of α-cyano-β-(2-nitro-4,5-dimethoxyphenyl)acrylamide (75.0g., 0.271 mole) in a 50% solution of acetic acid-N,N-dimethylformamide (750 ml.) at 75°C. When addition of the iron powder is complete, the mixture is heated to 90°C. for 4 hours and then filtered while hot. The filter cake is washed with hot acetic acid (150 ml.). The dark red filtrate is gradually added to IN hydrochloric acid (1500 ml.) and the pink precipitate recovered by filtration and recrystallized from an excess (10%) of aqueous sodium hydroxide. The solid is filtered, washed with cold isopropanol and dried to give the title product as yellow crystals. Yield = 57.1 g. (83.5%); mpp. 274°-275°C.

Workup

filtrationfiltered while hot
washThe filter cake is washed with hot acetic acid (150 ml.)
additionThe dark red filtrate is gradually added to IN hydrochloric acid (1500 ml.)
filtrationthe pink precipitate recovered by filtration
customrecrystallized from an excess (10%) of aqueous sodium hydroxide
filtrationThe solid is filtered
washwashed with cold isopropanol
customdried

Sources & evidence

ORD record: ord-5f23c007098249da9b1482b380cfbbf2
Source dataset: uspto-grants-1976_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03974161

Linked notes

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