4-[(3-Bromophenyl)amino]-6,7-dimethoxyquinoline-3-carbonitrile → 4-(3-Bromophenylamino)-6,7-dihydroxy-3-quinolinecarbonitrile

HRID 612207Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21]C)=[C:16]([O:19]C)[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:23]#[N:24])[CH:5]=[CH:6][CH:7]=1.Cl.N1C=CC=CC=1>[OH-].[NH4+]>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([OH:21])=[C:16]([OH:19])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:23]#[N:24])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 210 °C

Procedure

A stirred mixture of 4-(3-bromophenylamino)-6,7-dimethoxy-3-quinolinecarbonitrile (15.4 g, 40 mmol) and 100 g of pyridine hydrochloride was heated at 210° C. for 20 m, cooled to 0° C., treated with 100 ml of concentrated ammonium hydroxide, and concentrated to dryness. The residue was stirred with 1 L of water, and the resulting amber solid was filtered off, washed with water, and dried; mass spectrum (electrospray, m/e) M+H 356.1, 358.1.

Workup

temperaturecooled to 0° C.
concentrationconcentrated to dryness
filtrationthe resulting amber solid was filtered off
washwashed with water
customdried

Sources & evidence

ORD record: ord-abebf9e05d9447de9311cd0ed6bd32ba
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06002008

Reaction notes

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