Oxalyl chloride → 7-(Benzyloxy)-4-chloro-6-methoxyquinoline-3-carbonitrile

HRID 1595768Notes

Reaction equation

HRID 1595768 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](O)=[C:14]([C:19]#[N:20])[CH:15]=[N:16]2)=[CH:11][C:10]=1[O:22][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:27])=O>CCCCCC>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:27])=[C:14]([C:19]#[N:20])[CH:15]=[N:16]2)=[CH:11][C:10]=1[O:22][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 178486760HCID 178486760, compound

Product 1

HCID 224666467-(Benzyloxy)-4-chloro-6-methoxyquinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A total of 500 mg (1.63 mM) of 7-benzyloxy-4hydroxy-6-methoxy-quinoline-3-carbonitrile was taken up into 3 ml of oxalyl chloride (2M in CHCl3) and allowed to stand for 15 min followed by refluxing for 1 h. The solution was allowed to cool and then diluted with 300 mg of hexane to give a green solid. The solid was isolated and washed with excess hexane and dried under vacuum at 40° C. to yield 586 mg of 7-benzyloxy-4-chloro-6-methoxy-quinoline-3-carbonitrile as the hydrogen chloride salt. This compound was taken immediately on for the next step.

Workup

  1. temperatureby refluxing for 1 h
  2. temperatureto cool
  3. customto give a green solid
  4. customThe solid was isolated
  5. washwashed with excess hexane
  6. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-68ebd4705eef4322906fe6adecf7865d
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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