Sodium Hydroxide → HCID 57748331, compound

HRID 906189Notes

Reaction equation

HRID 906189 reaction equation
[Br:1][C:2]1[CH:12]=[C:11]([C:13]([NH2:15])=[O:14])[C:10]([NH:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[CH:9][C:3]=1[C:4]([O:6]CC)=[O:5].[OH-].[Na+]>CO>[NH2:15][C:13]([C:11]1[C:10]([NH:16][CH2:17][CH:18]([CH3:19])[CH3:20])=[CH:9][C:3]([C:4]([OH:6])=[O:5])=[C:2]([Br:1])[CH:12]=1)=[O:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67403041HCID 67403041, compound

Product 1

HCID 57748331HCID 57748331, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of ethyl 2-bromo-4-(aminocarbonyl)-5-[(2-methylpropyl)amino]benzoate (315 mg, 0.91 mmol) in methanol (20 mL) was added 1N aqueous sodium hydroxide (15 mL) and the mixture was stirred for 2 hr at 45° C. The mixture was then concentrated by rotary evaporation and diluted with water then adjusted to pH 2 by 1N aqueous hydrochloric acid addition and the mixture was allowed to stand for 1 hr at room temperature. The crystalline solid was collected by filtration and washed with water then dried to give 4-(aminocarbonyl)-2-bromo-5-[(2-methylpropyl)amino]benzoic acid (250 mg, 87.1%). MS (EI) for C12H15BrN2O3: 315.1 (MH+)

Workup

  1. concentrationThe mixture was then concentrated by rotary evaporation
  2. additiondiluted with water
  3. additionthen adjusted to pH 2 by 1N aqueous hydrochloric acid addition
  4. waitto stand for 1 hr at room temperature
  5. filtrationThe crystalline solid was collected by filtration
  6. washwashed with water
  7. customthen dried

Sources & evidence

ORD record
ord-a40d5be63d344a48a34ae78cbfd4b677
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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