Hydrogen Bromide → HCID 86605448, compound

HRID 1297105Notes

Reaction equation

HRID 1297105 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13].[BrH:20]>CS(C)=O.O>[NH2:1][C:2]1[C:7]([Br:20])=[C:6]([O:8][CH3:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 7148512HCID 7148512, compound

Product 1

HCID 86605448HCID 86605448, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 900 mg (3.5 mmol) of (2-amino-4,5-dimethoxyphenyl)(phenyl)methanone (XXIaa) in 60 ml of DMSO, add dropwise at 0° C. 15 g of HBr 40% by weight in water. Heat at 60° C. for 24 hours. Add 400 ml of H2O and extract four times with 200 ml of AcOEt; dry on MgSO4, evaporate the AcOEt and purify by silica chromatography (AcOEt 1/hexane 4). Yield: 65%. 1H-NMR (CDCl3, 300 MHz): d 3.67 (s, 3H, OCH3), 3.97 (s, 3H, OCH3), 6.59 (s, 2H, NH2), 7.06 (s, 1H Ar), 7.47–7.65 (m, 5H Ar). Mass: (M+H)+=335.98+337.98.

Workup

  1. extractionextract four times with 200 ml of AcOEt
  2. customdry on MgSO4
  3. customevaporate the AcOEt
  4. custompurify by silica chromatography (AcOEt 1/hexane 4)

Sources & evidence

ORD record
ord-b06aa9f1eb28488db53ff0f68980d160
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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