Dimethylformamide → HCID 21270414, compound

HRID 649597Notes

Reaction equation

HRID 649597 reaction equation
C(Cl)(=O)C([Cl:4])=O.CN(C=O)C.C(O)(C)C.C(=O)=O.[CH2:19]([O:26][C:27]([O:29][CH:30]1[CH2:39][CH2:38][C:37]2[N:36]=[CH:35][C:34]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[C:33](O)[C:32]=2[CH2:31]1)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[CH2:19]([O:26][C:27]([O:29][CH:30]1[CH2:39][CH2:38][C:37]2[N:36]=[CH:35][C:34]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[C:33]([Cl:4])[C:32]=2[CH2:31]1)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 86586944Isopropanol carbon dioxideHCID 178469471HCID 178469471, compound

Product 1

HCID 21270414HCID 21270414, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (1.82 g) is added to 100 mL of DMF dropwise under stirring and cooling (isopropanol-dry ice) maintaining the temperature below -20°. Stirring is continued for 30 minutes at the same temperature. To the mixture, 2.66 g of ethyl 6-benzyloxycarbonyloxy-4-hydroxy-5,6,7,8-tetrahydroquinoline-3-carboxylate is added in one portion, and stirring is continued for 2 hours at -30° to -20°, then at room temperature overnight. The reaction mixture is evaported to dryness and the residue is taken up in CH2Cl2, washed with saturated NaHCO3, dried (MgSO4) and evaporated to leave an oil which is purified by flash chromatography on a silica gel column obtaining ethyl 6-benzyloxycarbonyloxy-4-chloro-5,6,7,8-tetrahydroquinoline-3-carboxylate.

Workup

  1. temperaturemaintaining the temperature below -20°
  2. stirringStirring
  3. stirringstirring
  4. waitis continued for 2 hours at -30° to -20°
  5. customat room temperature
  6. customovernight
  7. washwashed with saturated NaHCO3
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customto leave an oil which
  11. customis purified by flash chromatography on a silica gel column

Sources & evidence

ORD record
ord-edd69df76f434880b8643753b3097abc
Source dataset
uspto-grants-1988_04
Patent number
US04740512

Reaction notes

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