Lithium Hydroxide → 4-(2-Carboxymethoxy-ethylamino)-3-nitro-benzoic acid

HRID 1629828Notes

Reaction equation

HRID 1629828 reaction equation
[N:1]1([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][C:9]=2[N+:18]([O-:20])=[O:19])[CH2:6][CH2:5][O:4][CH2:3][C:2]1=[O:7].[OH-:21].[Li+]>CO>[C:2]([CH2:3][O:4][CH2:5][CH2:6][NH:1][C:8]1[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[N+:18]([O-:20])=[O:19])([OH:21])=[O:7]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67049467Methyl 4-(morpholin-3-on-4-yl)-3-nitro-benzoate

Product 1

HCID 667319084-(2-Carboxymethoxy-ethylamino)-3-nitro-benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

400 mg (1.43 mmol) methyl 4-(morpholin-3-on-4-yl)-3-nitro-benzoate are dissolved in 15 ml of methanol and combined with 4.5 ml (4.5 mmol) 1-molar lithium hydroxide solution. The mixture is stirred for 2 hours at ambient temperature. Then it is evaporated down i. vac., the residue is diluted with water, cooled in the ice bath and acidified with 2-molar hydrochloric acid. After 10 minutes cooling in the ice bath the precipitate formed is filtered off, washed with water until neutral and dried at 50° C. in the drying cupboard.

Workup

  1. customThen it is evaporated down i
  2. addition, the residue is diluted with water
  3. temperaturecooled in the ice bath
  4. temperatureAfter 10 minutes cooling in the ice bath the precipitate
  5. customformed
  6. filtrationis filtered off
  7. washwashed with water until neutral and
  8. customdried at 50° C. in the drying cupboard

Sources & evidence

ORD record
ord-9179d167fff44d47b90f3534a8d7ceab
Source dataset
uspto-grants-2014_07
Patent number
US08791103B2

Reaction notes

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