Hydrochloric Acid → 4-(Aminocarbonyl)-5-(isopropylamino)-2-methylbenzoic acid

HRID 906162Notes

Reaction equation

HRID 906162 reaction equation
[NH2:1][C:2]([C:4]1[C:13]([NH:14][CH:15]([CH3:17])[CH3:16])=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[C:6]([CH3:18])[CH:5]=1)=[O:3].[OH-].[Na+].Cl>CO>[NH2:1][C:2]([C:4]1[C:13]([NH:14][CH:15]([CH3:16])[CH3:17])=[CH:12][C:7]([C:8]([OH:10])=[O:9])=[C:6]([CH3:18])[CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67402512Methyl 4-aminocarbonyl-5-(isopropylamino)-2-methylbenzoate

Product 1

HCID 577485914-(Aminocarbonyl)-5-(isopropylamino)-2-methylbenzoic acidYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-aminocarbonyl-5-(isopropylamino)-2-methylbenzoate (202 mg, 0.81 mmol) was dissolved in methanol (3 mL) and was treated with 1M sodium hydroxide (3 mL, 3 mmol) at 45° C. for 1.5 h. The reaction mixture was cooled to ambient temperature and 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 to afford 4-aminocarbonyl-5-(isopropylamino)-2-methylbenzoic acid (99.5 mg, 0.42 mmol, 52% yield). 1H NMR (400 MHz, d6-DMSO): δ 12.95 (br s, 1H), 7.90 (br s, 1H), 7.72 (d, 1H), 7.49 (s, 1H), 7.28 (br s, 1H), 7.06 (s, 1H), 3.64-3.54 (m, 1H), 2.33 (s, 3H), 1.15 (s, 3H), 1.14 (s, 3H); MS (EI) for C12H16N2O3: 237 (MH+).

Workup

  1. concentrationwas concentrated
  2. customto afford an aqueous residue that
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-e063932868504a07b2c1006021c69969
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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