Hydrochloric Acid → 5-Amino-4-carbamoyl-2-methylbenzoic acid

HRID 906182Notes

Reaction equation

HRID 906182 reaction equation
[NH2:1][C:2]1[C:3]([C:13]([NH2:15])=[O:14])=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+].Cl>CO>[NH2:1][C:2]1[C:3]([C:13](=[O:14])[NH2:15])=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67403771Methyl 5-amino-4-(aminocarbonyl)-2-methylbenzoate

Product 1

HCID 577483955-Amino-4-carbamoyl-2-methylbenzoic acidYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 5-amino-4-(aminocarbonyl)-2-methylbenzoate (108 mg, 0.52 mmol) was dissolved in methanol (1.5 mL) and was treated with 1 M sodium hydroxide (1.5 mL, 1.5 mmol) for 1 h. The reaction mixture was concentrated to afford an aqueous residue that was acidified with 1N hydrochloric acid to pH ˜3. The precipitate was collected by filtration, washed with water, and dried in vacuo to afford 5-amino-4-carbamoyl-2-methylbenzoic acid (60.8 mg, 0.31 mmol, 61% yield). 1H NMR (400 MHz, d6-DMSO): δ 12.95 (br s, 1H), 7.99 (br s, 1H), 7.52 (s, 1H), 7.42 (br s, 1H), 7.35 (s, 1H), 4.75 (br s, 2H), 2.33 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto afford an aqueous residue that
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-5c6fbb80b9994bbb8fdb393f6b0ab162
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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