Bromoacetic Acid → HCID 66747421, compound

HRID 1019985Notes

Reaction equation

HRID 1019985 reaction equation
Br[CH2:2][C:3]([OH:5])=[O:4].[CH3:6][O:7][C:8]1[C:9]([N+:17]([O-:19])=[O:18])=[C:10]([NH2:16])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]>>[CH3:6][O:7][C:8]1[C:9]([N+:17]([O-:19])=[O:18])=[C:10]([NH:16][CH2:2][C:3]([OH:5])=[O:4])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]

Participants

3

Reactant 2

HCID 6227Bromoacetic AcidHCID 10584093HCID 10584093, compound

Product 1

HCID 66747421HCID 66747421, compoundYield 68%

Conditions

Temperature
58 °C

Procedure

Bromoacetic acid (0.876 g, 6.31 mmol, 0.5 eq) is added portionwise to 3,4-dimethoxy-2-nitro-phenylamine (2.5 g, 12.61 mmol, 1.0 eq) and the mixture is stirred at 58° C. for 16 hours. The reaction is then quenched by 25% ammonia in water and diluted with water. The solid is filtered off and washed with 10% ammonia in water. The combined solutions are acidified by concentrated hydrochloric acid and the resulting precipitate is collected by filtration, washed with water and dried under vacuum to afford (3,4-dimethoxy-2-nitro-phenylamino)-acetic acid as a red solid (1.1 g, 34% yield).

Workup

  1. customThe reaction is then quenched by 25% ammonia in water
  2. additiondiluted with water
  3. filtrationThe solid is filtered off
  4. washwashed with 10% ammonia in water
  5. filtrationthe resulting precipitate is collected by filtration
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-23e169605e834739972f56fd7c3b89aa
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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