Oxalyl chloride → HCID 23087569, compound

HRID 1950073Notes

Reaction equation

HRID 1950073 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[CH:12]1[CH2:21][CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=2)[CH2:13]1)[CH3:2].[C:24](Cl)(=[O:28])[C:25](Cl)=[O:26]>C(OCC)C>[CH2:1]([N:3]1[C:4]2[C:9](=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=2[CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=3)[CH2:13]2)[C:25](=[O:26])[C:24]1=[O:28])[CH3:2]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 23087318Ethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine

Product 1

HCID 23087569HCID 23087569, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of ethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amine (260 mg) in diethyl ether (30 ml) was added dropwise oxalyl chloride (0.21 ml) on an ice bath, and the solution was stirred for 30 minutes at room temperature. The reaction solution was concentrated in vacuo, the total amount of the resulting {ethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amino}oxoacetyl chloride (crude product) was stirred in dichloromethane (5 ml), a solution of aluminum chloride (220 mg) in dichloromethane (20 ml) was added dropwise thereto on an ice bath, and the solution was stirred overnight at room temperature. The reaction mixture was diluted with ice water, extracted with chloroform, then washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (160 mg).

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. stirringthe total amount of the resulting {ethyl[5-methoxy-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenyl]amino}oxoacetyl chloride (crude product) was stirred in dichloromethane (5 ml)
  3. additiona solution of aluminum chloride (220 mg) in dichloromethane (20 ml) was added dropwise
  4. stirringon an ice bath, and the solution was stirred overnight at room temperature
  5. additionThe reaction mixture was diluted with ice water
  6. extractionextracted with chloroform
  7. washwashed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated in vacuo
  10. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-e4688862ae434c47864f843b4170beb4
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

Loading…