Hydrogen Bromide → HCID 22905643, compound

HRID 1488466Notes

Reaction equation

HRID 1488466 reaction equation
C([N:7]1[C:15]2[C:10](=[C:11]([CH3:19])[C:12]([O:17]C)=[C:13]([CH3:16])[CH:14]=2)[C:9]([CH3:21])([CH3:20])[CH2:8]1)(=O)C(C)(C)C.[BrH:22]>>[BrH:22].[OH:17][C:12]1[C:11]([CH3:19])=[C:10]2[C:15](=[CH:14][C:13]=1[CH3:16])[NH:7][CH2:8][C:9]2([CH3:20])[CH3:21]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 22905665HCID 22905665, compound

Product 1

HCID 22905643HCID 22905643, compoundYield 92%

Conditions

Temperature
100 °C

Procedure

In a round-bottom flask fitted with a reflux condenser were placed 19 (6 g, 20.8 mmol) and 49% hydrobromic acid (100 mL), and the mixture was heated at 100° C. for 18 h under a nitrogen atmosphere, and then cooled. The hydrobromic acid was removed under reduced pressure, and the resulting solid was washed with hexanes to yield 5-hydroxy-3,3,4,6-tetramethylindoline hydrobromide (5.2 g, 92% yield) as a colorless solid. Spectral data: 1H NMR (CD3OD): δ 1.50 (s, 6H), 2.25 (s, 3H), 2.30 (s, 3H), 3.50 (s, 2H), 7.00 (s, 1H); 13C NMR (CD3OD): δ 12.0, 17.1, 26.6, 44.6, 59.9, 119.2, 123.2, 126.7, 127.1, 140.6, 156.2.

Workup

  1. customIn a round-bottom flask fitted with a reflux condenser
  2. temperaturecooled
  3. customThe hydrobromic acid was removed under reduced pressure
  4. washthe resulting solid was washed with hexanes

Sources & evidence

ORD record
ord-e24542f672f8455aa81028b6138ac3b5
Source dataset
uspto-grants-1997_10
Patent number
US05674876

Reaction notes

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