Acetic Anhydride → 1-(4-Hydroxy-2-methyl-3,4-dihydro-2H-quinolin-1-yl)-ethanone

HRID 1796692Notes

Reaction equation

HRID 1796692 reaction equation
[CH3:1][CH:2]1[CH2:11][CH:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[C:13](OC(=O)C)(=[O:15])[CH3:14]>ClCCl>[OH:12][CH:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]([C:13](=[O:15])[CH3:14])[CH:2]([CH3:1])[CH2:11]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 1476341,2,3,4-Tetrahydro-2-methyl-4-quinolinol

Product 1

HCID 221825571-(4-Hydroxy-2-methyl-3,4-dihydro-2H-quinolin-1-yl)-ethanoneYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,2,3,4-tetrahydro-2-methyl-4-quinolinol (5.9 g, 36.4 mmol) and acetic anhydride (37.1 g, 364 mmol) in dichloromethane (100 ml) was stirred for one hour. The solvents were evaporated and the crude product was purified on silica (ethyl acetate:heptane 1:1) to obtain the sub-titled product (33.5 mmol).

Workup

  1. customThe solvents were evaporated
  2. customthe crude product was purified on silica (ethyl acetate:heptane 1:1)

Sources & evidence

ORD record
ord-32e070209f194d69add2ef3a195f8a6a
Source dataset
uspto-grants-2006_04
Patent number
US07030246B2

Reaction notes

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