Acetic Anhydride → 1-Acetyl-5-hydroxy-6-trifluoromethylindoline

HRID 840545Notes

Reaction equation

HRID 840545 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])[NH:7][CH2:6][CH2:5]2.[C:15](OC(=O)C)(=[O:17])[CH3:16]>ClCCl>[C:15]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([OH:1])=[C:10]([C:11]([F:14])([F:12])[F:13])[CH:9]=2)[CH2:5][CH2:6]1)(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 226198656-(Trifluoromethyl)indolin-5-ol

Product 1

HCID 226198641-Acetyl-5-hydroxy-6-trifluoromethylindolineYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of indoline (D4, 2.84 g, 14 mmol) and acetic anhydride (1.32 ml, 14 mmol) in dry dichloromethane (50 ml) was stirred at room temperature for 3 h, then evaporated. The residue was treated cautiously with saturated sodium bicarbonate solution, then the solid product was filtered off, washed with water and dried to give the title compound (3.28 g, 96%), m.p. 244-7° C.

Workup

  1. customevaporated
  2. additionThe residue was treated cautiously with saturated sodium bicarbonate solution
  3. filtrationthe solid product was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-c89ec8ac07fb41f9b4987d9786e71ae6
Source dataset
uspto-grants-2002_04
Patent number
US06369060B1

Reaction notes

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