Acetic Anhydride → 1-Acetyl-6-hydroxymethyl-1,2,3,4-tetrahydroquinoline

HRID 1604586Notes

Reaction equation

HRID 1604586 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7][CH2:6]2.[C:13](OC(=O)C)(=[O:15])[CH3:14]>CO>[C:13]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([CH2:2][OH:1])=[CH:12][CH:11]=2)[CH2:6][CH2:7][CH2:8]1)(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 226628871,2,3,4-Tetrahydroquinolin-6-ylmethanol

Product 1

HCID 212548181-Acetyl-6-hydroxymethyl-1,2,3,4-tetrahydroquinolineYield 57.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-hydroxymethyl-1,2,3,4-tetrahydroquinoline (314 mg) in methanol (4 ml) was dropwise added acetic anhydride (589 mg) under ice-cooling, and the mixture was stirred for 1 hour at the same temperature. The solvent was removed in vacuo, and ethyl acetate and saturated sodium bicarbonate solution was added to the residue. The organic layer was washed with water and brine, dried and concentrated in vacuo. The residue was purified by preparative thin-layer chromatography (n-hexane:ethyl acetate=1:2, V/V) to give 1-acetyl-6-hydroxymethyl-1,2,3,4-tetrahydroquinoline (227 mg) as powder.

Workup

  1. temperaturecooling
  2. customThe solvent was removed in vacuo, and ethyl acetate and saturated sodium bicarbonate solution
  3. additionwas added to the residue
  4. washThe organic layer was washed with water and brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative thin-layer chromatography (n-hexane:ethyl acetate=1:2, V/V)

Sources & evidence

ORD record
ord-9b0a7e500b5740508254bbe4ab955108
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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