N-Acetyl-5-methoxy-3,3,4,6-tetramethylindoline → 1-Acetyl-3,3,4,6-tetramethyl-5-indolinol

HRID 1488464Notes

Reaction equation

HRID 1488464 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:16])[C:9]([O:14]C)=[C:10]([CH3:13])[CH:11]=2)[C:6]([CH3:18])([CH3:17])[CH2:5]1)(=[O:3])[CH3:2].C(N1C2C(=C(C)C(O)=C(C)C=2)C(C)C1)(=O)C>>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:16])[C:9]([OH:14])=[C:10]([CH3:13])[CH:11]=2)[C:6]([CH3:18])([CH3:17])[CH2:5]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 22905632N-Acetyl-5-methoxy-3,3,4,6-tetramethylindolineHCID 22905640N-Acetyl-5-hydroxy-3,4,6-trimethylindoline

Product 1

HCID 3823271-Acetyl-3,3,4,6-tetramethyl-5-indolinolYield 75%

Procedure

Treatment of 15 (741 mg, 3 mmol) according to a procedure similar that used for making 11a afforded 16 (524 mg, 75% yield) as a colorless solid, mp 173°-174° C. Spectral data: 13C NMR (CD3 SOCD3): δ 11.7, 17.3, 23.9, 27.0, 40.6, 63.7, 115.4, 121.1, 122.8, 135.6, 149.2, 167.2; HRMS: calcd. for C14H19NO2 233.1415, fnd. 233.1416. Anal: calcd. for C14H19NO2C, 72.08, N, 6.00, H, 8.20, fnd. C, 71.88, N, 5.95, H, 8.22.

Sources & evidence

ORD record
ord-1a0db94f8d7c439aba5aabe6db0ee7b2
Source dataset
uspto-grants-1997_10
Patent number
US05674876

Reaction notes

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