Isatin → Indol-2-one, 3-(3,5-dimethylphenyl)-3-hydroxy-1,3-dihydro-

HRID 1297760Notes

Reaction equation

[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].[CH3:12][C:13]1[CH:14]=[C:15]([Mg]Br)[CH:16]=[C:17]([CH3:19])[CH:18]=1>>[CH3:12][C:13]1[CH:14]=[C:15]([C:4]2([OH:5])[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:1][C:2]2=[O:3])[CH:16]=[C:17]([CH3:19])[CH:18]=1

Participants

Reactant 2

HCID 7054Isatin

HCID 178425074HCID 178425074, compound

Product 1

HCID 5297657Indol-2-one, 3-(3,5-dimethylphenyl)-3-hydroxy-1,3-dihydro-Yield 81.3%

Procedure

Using a method similar to Preparation 18 with isatin (1.47 g, 10 mmol) and 3,5-dimethylphenylmagnesium bromide (0.5M in THF, 42 mL, 21 mmol) gave 2.06 g (81%) of the title compound as a peach-color solid. MS (ES): m/z=236 (M+1−H2O), 252 (M−1); 1H NMR(DMSO-d6): δ10.34 (s, 1H), 7.23 (dt, J=1.3 Hz, J=7.6 Hz, 1H), 7.07 (d, J=6.7 Hz, 1H), 6.95 (dt, J=0.9 Hz, J=7.4 Hz, 1H), 6.88 (m, 4H), 6.51 (s, 1H), 2.21 (s, 6H).

Sources & evidence

ORD record: ord-a11c5f758e014ee39194a428843f8055
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250442B2

Reaction notes

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