O-Toluidine → HCID 131733192, compound

HRID 2206474Notes

Reaction equation

HRID 2206474 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[CH:14]O)[C:9]([O:11][CH2:12][CH3:13])=[O:10].[NH2:16][C:17]1[C:18]([CH3:23])=[CH:19][CH:20]=[CH:21][CH:22]=1>CO>[C:18]1([CH3:23])[C:17]([NH:16][CH:14]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 89739510HCID 89739510, compound

Product 1

HCID 131733192HCID 131733192, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-(2-bromophenyl)-3-hydroxyacrylate (1 g, 3.88 mmol) in methanol (10 mL) was added o-toluidine (0.416 g, 3.88 mmol) via syringe at room temperature. After being stirred for 18 hours at the same temperature, solvent was removed under reduced pressure to give the crude product of ethyl 3-(o-toluidino)-2-(2-bromophenyl)acrylate (1.326 g, 95%), which was used in the next step without further purification. LRMS (M+H) m/z: calcd 359.05. found 359.

Workup

  1. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-9dd14211ab344bd4bc7442717b81a3f7
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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