Potassium Hydroxide → 4-[Ethyl-(3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid

HRID 2290133Notes

Reaction equation

HRID 2290133 reaction equation
C([O:3][C:4](=[O:28])[C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH2:26][CH3:27])[C:12]2[CH:13]=[C:14]([CH:23]([CH3:25])[CH3:24])[C:15]3[O:19][CH2:18][C:17]([CH3:21])([CH3:20])[C:16]=3[CH:22]=2)=[CH:7][CH:6]=1)C.[OH-].[K+]>C(O)C>[CH2:26]([N:11]([C:12]1[CH:13]=[C:14]([CH:23]([CH3:24])[CH3:25])[C:15]2[O:19][CH2:18][C:17]([CH3:20])([CH3:21])[C:16]=2[CH:22]=1)[C:8]1[CH:7]=[CH:6][C:5]([C:4]([OH:28])=[O:3])=[CH:10][CH:9]=1)[CH3:27]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 154540924-[Ethyl-(3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl ester2×

Product 1

HCID 99284994-[Ethyl-(3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acidYield 91.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following general procedure I and using 4-[ethyl-(3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl ester (Compound 24, 0.045 g, 0.117 mmol) and 2 mL of 5M potassium hydroxide solution in 20 mL of ethanol, the title compound (0.038 g, 86%) was obtained as a white solid. 1H NMR (300 MHz, CDCl3): δ 7.80 (d, 2H, J=9.0 Hz), 6.74 (d, 1H, J=2.1 Hz), 6.67 (d, 1H, J=2.1 Hz), 6.50 (d, 2H, J=9.0 Hz), 4.21 (s, 2H), 3.66 (q, 2H, J=7.2 Hz), 3.01 (heptet, 1H J=7.0 Hz), 1.26 (s, 6H), 1.18 (t, 3H J=7.2 Hz), 1.16 (d, 6H, J=7.0 Hz).

Sources & evidence

ORD record
ord-fa6a2d53d9134f479cc73765ca5b31ba
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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