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

HRID 2290143Notes

Reaction equation

HRID 2290143 reaction equation
C([O:3][C:4](=[O:29])[C:5]1[CH:10]=[CH:9][C:8](N(C(C)C)C2C=C(C(C)C)C3OCC(C)(C)C=3C=2)=[CH:7][CH:6]=1)C.[CH3:30][C:31]1([CH3:47])[C:35]2[CH:36]=[C:37]([NH:43][CH:44]([CH3:46])[CH3:45])[CH:38]=[C:39]([CH:40]([CH3:42])[CH3:41])[C:34]=2[O:33][CH2:32]1.[OH-].[Na+]>C(O)C>[CH:44]([N:43]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:4]([OH:29])=[O:3])[C:37]1[CH:38]=[C:39]([CH:40]([CH3:42])[CH3:41])[C:34]2[O:33][CH2:32][C:31]([CH3:30])([CH3:47])[C:35]=2[CH:36]=1)([CH3:46])[CH3:45]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 186991783,3-Dimethyl-7-isopropyl-5-(isopropyl)amino-2,3-dihydro-benzofuran2×HCID 539697824-[Isopropyl-(3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl ester2×

Product 1

HCID 18699192[Isopropyl-(3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acidYield 13.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following general procedure I and using 4-[isopropyl-(3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl ester [(Compound 39, 0.15 g, contaminated with 3,3-dimethyl-7-isopropyl-5-(isopropyl)amino-2,3-dihydro-benzofuran (Compound 35)] and 2 mL of 5M sodium hydroxide in 10 mL of ethanol, the title compound (0.043 g, 13.4% for 2 steps) was obtained as a white solid. 1H NMR (300 MHz, CDCl3): δ 7.86 (d, 2H, J=9.0 Hz), 6.71 (d, 1H, J=2.0 Hz), 6.64 (d, 1H, J=2.0 Hz), 6.51 (d, 2H, J=9.0 Hz), 4.36 (heptet, 1H, J=6.4 Hz), 4.30 (s, 2H), 3.09 (heptet, 1H, J=6.9 Hz), 1.33 (s, 6H), 1.23 (d, 6H, J=6.9 Hz), 1.15 (d, 6H, J=6.4 Hz).

Sources & evidence

ORD record
ord-8dfda5a28c5e4102a48b8e86efaec2a2
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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