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

HRID 548476Notes

Reaction equation

HRID 548476 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.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CN(C)C=O>[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

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 178486760HCID 178486760, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 1 g of 7-benzyloxy-4-hydroxy-6-methoxy-quinoline-3-carbonitrile in 10 ml of methylene chloride was added 5 ml of oxalyl chloride (2M in methylene chloride), and 2 drops of N,N-dimethylformamide. The mixture was refluxed for 20 min and to it was slowly added aqueous sodium bicarbonate until the bubbling ceased. Following separation of the layers, the organic layer was evaporated to a small volume, then passed through a plug of magnesol. Elution with 50 ml methylene chloride, followed by evaporation provided 0.6 g of 7-benzyloxy-4-chloro-6-methoxy-quinoline-3-carbonitrile as a pale yellow solid, mp 282-284° C.; mass spectrum (electrospray, m/e) M+H 325.

Workup

  1. temperatureThe mixture was refluxed for 20 min and to it
  2. customseparation of the layers
  3. customthe organic layer was evaporated to a small volume
  4. washElution with 50 ml methylene chloride
  5. customfollowed by evaporation

Sources & evidence

ORD record
ord-09ef4e16cf6b4b1f95c654c446638786
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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