Sodium Hydroxide → 4-[[(1,1-Dimethyl-3-phenyl-1H-inden-5-yl)amino]carbonyl]benzoic acid

HRID 53283Notes

Reaction equation

HRID 53283 reaction equation
[CH3:1][C:2]1([CH3:30])[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=3)=[O:13])=[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+]>O1CCCC1.CO>[CH3:1][C:2]1([CH3:30])[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)=[O:13])=[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

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19034440Methyl 4-[[(1,1-dimethyl-3-phenyl-1H-inden-5-yl)amino]carbonyl]benzoate

Product 1

HCID 199622234-[[(1,1-Dimethyl-3-phenyl-1H-inden-5-yl)amino]carbonyl]benzoic acidYield 78.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-[[(1,1-dimethyl-3-phenyl-1H-inden-5-yl)amino]carbonyl]benzoate (325 mg, 0.82 mmol), 4.1 mL of 2N NaOH in 10 mL of tetrahydrofuran and 10 mL of methanol were stirred for 2 hours. The mixture was concentrated and acidified with 1N HCl (20 mL), extracted with ethyl acetate (35 mL×2). The combined extracts were washed with water (10 mL), dried over magnesium sulfate, and evaporated. The residue was triturated in ether-hexane to give 246 mg (78% yield) of the title compound as white solids; NMR (DMSO-d6) δ1.35 (s, 6H), 6.58 (s, 1H), 7.38-7.70 (m, 7H), 7.73 (d, J=7.9 Hz, 1H), 7.90 (s, 1H), 8.04 (s, 4H), 10.38 (bs, 1H), 13.25 (bs, 1H); MS m/e 384 (MH+).

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted with ethyl acetate (35 mL×2)
  3. washThe combined extracts were washed with water (10 mL)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was triturated in ether-hexane

Sources & evidence

ORD record
ord-abf8a50ec94047e1bf23826b5a87330e
Source dataset
uspto-grants-1997_04
Patent number
US05618839

Reaction notes

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