Sodium Bicarbonate → HCID 21277152, compound

HRID 2292355Notes

Reaction equation

HRID 2292355 reaction equation
Br.[NH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([OH:14])[CH:8]=1)=[O:5].C(=O)(O)[O-].[Na+]>O>[NH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([OH:14])[CH:8]=1)=[O:5]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 21277151HCID 21277151, compound

Product 1

HCID 21277152HCID 21277152, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 26.2 g (76.2 mmol) of [2-[(3,4-dimethoxyphenyl)amino]-2-oxoethyl]carbamic acid in 1 liter of absolute dichloromethane was added dropwise at -60° C. 63.1 g of boron tribromide. After stirring overnight at room temperature, 180 ml of water was added at 0° C. The resulting precipitate was filtered off and dried in vacuo. To a solution of 26.1 g of crude 2-amino-N-(3,4-dihydroxyphenyl)acetamide hydrobromide salt in 600 ml of methanol was added 8 ml of concentrated hydrochloric acid and the mixture was refluxed for 1 hour. Evaporation to dryness yielded 16.5 g of the hydrobromide salt of 2-amino-N-(3,4-dihydroxyphenyl)acetamide. To a solution of 15.4 g of 2-amino-N-(3,4-dihydroxyphenyl)acetamide hydrobromide salt in 175 ml of water was added sodium bicarbonate until the pH reached 6.7. The resulting precipitate was filtered off with suction and dried in vacuo; yield: 10.5 g.

Workup

  1. filtrationThe resulting precipitate was filtered off with suction
  2. customdried in vacuo

Sources & evidence

ORD record
ord-c9a3575cebcf4261891382603e07baf7
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

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