Ammonia → Methyl 7-aminofuro[2,3-c]quinoline-6-carboxylate

HRID 1778344Notes

Reaction equation

[NH2:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([N+:12]([O-])=O)[C:5]([C:15]2[CH:19]=[CH:18][O:17][C:16]=2[CH:20]=O)=[CH:4][CH:3]=1.CO.N>Cl.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2]>[NH2:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]2[C:5]([C:15]3[CH:19]=[CH:18][O:17][C:16]=3[CH:20]=[N:12]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

1M Hydrochloric acid (14 drops) was added to a solution of iron (II) sulfate heptahydrate (18.44 g) in water (50 mL) and the resultant solution was added to methyl 6-amino-3-(2-formylfuran-3-yl)-2-nitrobenzoate (Intermediate 30, 2.02 g). The resultant mixture was stirred and heated at reflux for 10 minutes then cooled to 70° C. Methanol (50 mL) was added followed by aqueous ammonia (33%, 19.2 mL) and the mixture was stirred and heated at reflux for 5 hours. After cooling, methanol (50 mL) was added and the mixture was filtered through Celite and the filtrate was evaporated to dryness. The residue was purified by chromatography on silica, eluting with a DMAW 350 followed by DMAW 240 and DMAW 120 to give methyl 7-aminofuro[2,3-c]quinoline-6-carboxylate (0.27 g) as a brown solid.

Workup

temperatureheated
temperatureat reflux for 10 minutes
temperatureheated
temperatureat reflux for 5 hours
temperatureAfter cooling
filtrationthe mixture was filtered through Celite
customthe filtrate was evaporated to dryness
customThe residue was purified by chromatography on silica
washeluting with a DMAW 350

Sources & evidence

ORD record: ord-a6a44e5a4fea45c99e4c5d494b3cd6aa
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266896B2

Reaction notes

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