Oxalyl chloride → Ethyl 6-benzyloxy-4-chloro-6-methyl-5,6,7,8-tetrahydroquinoline-3-carboxylate

HRID 1905706Notes

Reaction equation

HRID 1905706 reaction equation
C(Cl)(=O)C([Cl:4])=O.[CH2:7]([O:14][C:15]1([CH3:31])[CH2:24][CH2:23][C:22]2[N:21]=[CH:20][C:19]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:18](O)[C:17]=2[CH2:16]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CN(C=O)C>[CH2:7]([O:14][C:15]1([CH3:31])[CH2:24][CH2:23][C:22]2[N:21]=[CH:20][C:19]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:18]([Cl:4])[C:17]=2[CH2:16]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 178469467HCID 178469467, compound

Product 1

HCID 21270424Ethyl 6-benzyloxy-4-chloro-6-methyl-5,6,7,8-tetrahydroquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Oxalyl chloride (5.2 g) is added to 200 mL of DMF dropwise under stirring and cooling keeping the temperature below -20°. Stirring is continued for 0.5 hour at the same temperature. To the mixture 7.0 g of ethyl 6-benzyloxy-4-hydroxy-6-methyl-5,6,7,8-tetrahydroquinoline-3-carboxylate is added in small portions and stirring is continued for 2 hours at -30° to -20°, then at room temperature overnight. The mixture is evaporated to dryness and the residue is taken up in CH2Cl2, washed with sat. NaHCO3, dried (MgSO4) and evaporated to dryness to an oil which is chromatographed on silica gel to yield ethyl 6-benzyloxy-4-chloro-6-methyl-5,6,7,8-tetrahydroquinoline-3-carboxylate.

Workup

  1. temperaturecooling
  2. customthe temperature below -20°
  3. stirringStirring
  4. stirringstirring
  5. waitis continued for 2 hours at -30° to -20°
  6. customat room temperature
  7. customovernight
  8. customThe mixture is evaporated to dryness
  9. washwashed with sat. NaHCO3
  10. dry with materialdried (MgSO4)
  11. customevaporated to dryness to an oil which
  12. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-9f1d5749376e4ebcb5601230b3bb38dc
Source dataset
uspto-grants-1987_03
Patent number
US04647566

Reaction notes

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