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

HRID 2290132Notes

Reaction equation

HRID 2290132 reaction equation
C([O:3][C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH3:26])[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>[CH3:26][N:11]([C:12]1[CH:13]=[C:14]([CH:23]([CH3:25])[CH3:24])[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:27])=[O:3])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 154540914-[Methyl-(3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl ester2×

Product 1

HCID 98627344-[Methyl-(3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acidYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following general procedure I and using 4-[methyl-(3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl ester (Compound 23, 0.03 g, 0.081 mmol) and 2 mL of 5M potassium hydroxide solution in 10 mL of ethanol, the title compound (0.022 g, 79%) was obtained as a white solid. 1H NMR (300 MHz, CDCl3): δ 7.90 (d, 2H, J=9.0 Hz), 6.85 (d, 1H, J=2.2 Hz), 6.78 (d, 1H, J=2.2 Hz), 6.63 (d, 2H, J=9.0 Hz), 4.27 (s, 2H), 3.33 (s, 3H), 3.09 (heptet, 1H, J=6.8 Hz), 1.33 (s, 6H), 1.23 (d, 6H, J=6.8 Hz).

Sources & evidence

ORD record
ord-c74778e13c5040f487d2d7eb1ba4c62b
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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