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

HRID 427731Notes

Reaction equation

HRID 427731 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 (D10, 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-876558b988474832b13e3a1f1af31336
Source dataset
uspto-grants-2001_11
Patent number
US06313145B1

Reaction notes

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