Boron tribromide → HCID 135525315, compound

HRID 1455504Notes

Reaction equation

[C:1]1([NH:7][C:8]([C:10]2[C:11]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:29])=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[C:15]([O:20]C)[CH:14]=3)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B(Br)(Br)Br>C(Cl)Cl>[C:1]1([NH:7][C:8]([C:10]2[C:11]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:29])=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[C:15]([OH:20])[CH:14]=3)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: -78 °C

Procedure

2-(2-Chloro-phenylamino)-7-methoxy-quinoline-3-carboxylic acid phenylamide (404 mg, 1.0 mmol) was dissolved in dry CH2Cl2 (5 ml). After cooling to −78° C., 1.0 N BBr3 (5.0 ml, 5.0 mmol) in CH2Cl2 was dropped into the above solution over 5 min. The reaction mixture was allowed to warm to room temperature over 1 hr and stirred for 5 days. CH2Cl2 was added to extract the reaction mixture, and washed with water, saturated brine and then dried with magnesium sulfate. After evaporating the solvent under reduced pressure, the residue was purified by chromatography on SCX column using MeOH as eluent. At last, 2-(2-Chloro-phenylamino)-7-hydroxy-quinoline-3-carboxylic acid phenylamide was obtained as yellow solid after recrystallization from CH2Cl2 and Hexane; 210 mg (54%).

Workup

temperatureto warm to room temperature over 1 hr
extractionto extract the reaction mixture
washwashed with water, saturated brine
dry with materialdried with magnesium sulfate
customAfter evaporating the solvent under reduced pressure
customthe residue was purified by chromatography on SCX column

Sources & evidence

ORD record: ord-59933c7bbbe245c0bebaa7f63c1755fb
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07482455B2

Reaction notes

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