Hydrochloric Acid → 4-[(1,1-Dimethyl-3-phenyl-1H-indene-5-carbonyl)amino]benzoic acid

HRID 53281Notes

Reaction equation

HRID 53281 reaction equation
[CH3:1][C:2]1([CH3:30])[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH:13][C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=3)=[O:12])=[CH:8][CH:9]=2)[C:4]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:3]1.[OH-].[Na+].Cl>CO.O1CCCC1>[CH3:1][C:2]1([CH3:30])[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH:13][C:14]3[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)=[O:12])=[CH:8][CH:9]=2)[C:4]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19034396Methyl 4-[(1,1-dimethyl-3-phenyl-1H-indene-5-carbonyl)amino]benzoate

Product 1

HCID 190343904-[(1,1-Dimethyl-3-phenyl-1H-indene-5-carbonyl)amino]benzoic acidYield 94.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-[(1,1-dimethyl-3-phenyl-1H-indene-5-carbonyl)amino]benzoate (359 mg, 0.90 mmol) was stirred with 4.5 mL of 2N NaOH in 5 mL of methanol and 5 mL of tetrahydrofuran for 10 hours. The solution was acidified with 1N HCl and concentrated under reduced pressure. After addition of 15 mL of water, the mixture was extracted with ethyl acetate (15 mL×3). The combined extracts were washed with water (10 mL), dried over magnesium sulfate, and evaporated. The residue was triturated in etherhexane to give 326 mg (94% yield) of the title compound as solids; 1H-NMR (DMSO-d6) δ1.39 (s, 6H), 6.68 (s, 1H), 7.39-7.53 (m, 3H), 7.64-7.68 (m, 3H), 7.85-7.97 (m, 6H), 10.54 (s, 1H), 12.75 (bs, 1H); MS m/e 384 (MH+).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionAfter addition of 15 mL of water
  3. extractionthe mixture was extracted with ethyl acetate (15 mL×3)
  4. washThe combined extracts were washed with water (10 mL)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was triturated in etherhexane

Sources & evidence

ORD record
ord-272057e051464e78abd563c979cf05f9
Source dataset
uspto-grants-1997_04
Patent number
US05618839

Reaction notes

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