3-(3-Benzyloxy-4-bromo-phenylamino)-but-2-enoic acid ethyl ester → 7-Benzyloxy-6-bromo-2-methyl-quinolin-4-ol

HRID 1374778Notes

Reaction equation

C(O[C:4](=[O:24])[CH:5]=[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[C:11]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:10]=1)[CH3:7])C>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[CH2:17]([O:16][C:11]1[CH:10]=[C:9]2[C:14]([C:4]([OH:24])=[CH:5][C:6]([CH3:7])=[N:8]2)=[CH:13][C:12]=1[Br:15])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 250 °C

Procedure

Dowtherm®A (320 mL) was heated to 250° C. then a solution of 3-(3-benzyloxy-4-bromo-phenylamino)-but-2-enoic acid ethyl ester (55.5 g, 99.5 mmol) in Dowtherm®A (120 mL) was slowly added. The reaction mixture was heated 16 min at 250° C. and ethanol was collected by distillation. The mixture was cooled down, diluted with hexanes (1.5 L) and filtered. The solid was washed with ether and dried under vacuum. 73.0 g of the title compound were obtained. Brown solid, ISP-MS: m/e=345.2 ([M+H]+).

Workup

distillationethanol was collected by distillation
temperatureThe mixture was cooled down
additiondiluted with hexanes (1.5 L)
filtrationfiltered
washThe solid was washed with ether
customdried under vacuum

Sources & evidence

ORD record: ord-b4c1db73d1764be89f7ae82b6fb9e9b4
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07166589B2

Reaction notes

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