Oxalyl chloride → Methyl 3-methyl-2-phenylquinoline-4-carboxylate
Reaction equation
[CH3:1][C:2]1[C:3]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:4][C:5]2[C:10]([C:11]=1[C:12]([OH:14])=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:21](Cl)(=O)C(Cl)=O>C(Cl)Cl.CN(C=O)C>[CH3:21][O:13][C:12]([C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[C:3]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:2]=1[CH3:1])=[O:14]Participants
Procedure
30 g (114 mmol) of 3-methyl-2-phenylquinoline-4-carboxylic acid (CAS [43071-45-0]) were suspended in 250 ml of dry CH2Cl2; 20 ml (230 mmol) of oxalyl chloride dissolved in 120 ml of CH2Cl2 were added dropwise and the reaction mixture was stirred at room temperature for 30 min. Two drops of DMF were added and the reaction was stirred for additional 30 min. The solvent was evaporated in vacuo to dryness, the residue was taken up with 100 ml of CH2Cl2 and 100 ml of MeOH, dissolved in 400 ml of CH2Cl2, were added dropwise. After stirring for 18 h the solvent was evaporated in vacuo to dryness, the residue was taken up with CH2Cl2 and washed with 1% NaHCO3; the organic layer was dried over anhydrous Na2SO4, filtered and evaporated in vacuo to dryness to yield 31.6 g of the title compound as a solid, which was used in the following reaction without further purification.
Workup
- additionwere added dropwise
- stirringthe reaction was stirred for additional 30 min
- customThe solvent was evaporated in vacuo to dryness
- dissolutiondissolved in 400 ml of CH2Cl2
- additionwere added dropwise
- stirringAfter stirring for 18 h the solvent
- customwas evaporated in vacuo to dryness
- washwashed with 1% NaHCO3
- dry with materialthe organic layer was dried over anhydrous Na2SO4
- filtrationfiltered
- customevaporated in vacuo to dryness
Sources & evidence
- ORD record
- ord-5655313579d74ca19616e6049c2fa73b
- Source dataset
- uspto-grants-2003_09
- Patent number
- US06613770B1
Reaction notes
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