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

HRID 265442Notes

Reaction equation

HRID 265442 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 ether-hexane to give 326 mg (94% yield) of the title compound as solids; 1H-NMR (DMSO-d6) δ 1.39 (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 ether-hexane

Sources & evidence

ORD record
ord-250ca9f888534fc787b9e4afcb743a52
Source dataset
uspto-grants-1997_07
Patent number
US05648385

Reaction notes

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