Sodium Hydroxide → HCID 9819947, compound

HRID 2290167Notes

Reaction equation

C([O:3][C:4](=[O:28])[C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH2:25][CH2:26][CH3:27])[C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[C:17]([CH3:22])([CH3:21])[O:16][C:15]3([CH3:24])[CH3:23])=[CH:7][CH:6]=1)C.[OH-].[Na+]>C(O)C>[CH2:25]([N:11]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[C:17]([CH3:22])([CH3:21])[O:16][C:15]2([CH3:23])[CH3:24])[C:8]1[CH:7]=[CH:6][C:5]([C:4]([OH:28])=[O:3])=[CH:10][CH:9]=1)[CH2:26][CH3:27]

Participants

Conditions

Temperature: 55 °C

Procedure

A solution of 4-[n-propyl-(1,1,3,3-tetramethyl-1,3-dihydro-isobenzofuran-5-yl)-amino]-benzoic acid ethyl ester (Compound 81, 0.22 g, 0.58 mmol) in 20 mL of ethanol was treated with 2 mL of 5M sodium hydroxide solution and the resulting solution was heated at 55° C. for 2 hours. The volatiles were removed by distillation in vacuo and the residue was acidified using hydrochloric acid and extracted with ethyl acetate. The organic extract was washed with brine, dried over anhydrous sodium sulfate and evaporated to a residue which was recrystallized from hot ethyl acetate to afford the title compound (0.12 g, 55%) as a white solid. 1H NMR (300 MHz, acetone-d6): δ 7.80 (d, 2H, J=9.0 Hz), 7.28 (d, 1H, J=8.0 Hz), 7.04 (dd, 1H, J=8.0,1.8 Hz), 7.10 (d, 1H, J=1.8 Hz), 6.72 (d, 2H, J=8.9 Hz), 3.73 (t, 2H, J=7.8 Hz), 1.76-1.64 (m, 2H), 1.48 (s, 6H), 1.46 (s, 6H), 0.94 (t, 3H, J=7.4 Hz).

Workup

customThe volatiles were removed by distillation in vacuo
extractionextracted with ethyl acetate
extractionThe organic extract
washwas washed with brine
dry with materialdried over anhydrous sodium sulfate
customevaporated to a residue which
customwas recrystallized from hot ethyl acetate

Sources & evidence

ORD record: ord-eb5a83e5209d47c29cc66f5f814aa72f
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093838

Reaction notes

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