Methanol → Methyl 6-quinolineacetate

HRID 655216Notes

Reaction equation

HRID 655216 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][C:12]([OH:14])=[O:13])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.OS(O)(=O)=O.[CH3:20]O>ClCCl>[CH3:20][O:13][C:12](=[O:14])[CH2:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[CH:4]2

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 117887092-(Quinolin-6-yl)acetic acid

Product 1

HCID 1514202Methyl 6-quinolineacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of quinolin-6-yl-acetic acid (10 g, 53.0 mmol) in 100 ml of methanol was added 2.5 ml of concentrated H2SO4 The mixture was heated to reflux for 3 hours. The reaction mixture was concentrated to give a brown residue, which was diluted with 100 ml of dichloromethane, washed with sat. aq. NaHCO3 and brine, then the organic layer was dried over anhydrous Na2SO4 and concentrated to return the title compound as a brown oil (7.9 g, 73.6%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated
  4. customto give a brown residue, which
  5. washwashed with sat. aq. NaHCO3 and brine
  6. dry with materialthe organic layer was dried over anhydrous Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7247593a5e0b47cda89049d9fa8b565d
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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