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Butanoic acid, 4-chloro-4-oxo-, methyl ester → 8-[2,6-Dichloro-3-(3-methoxycarbonylpropionylamino)benzyloxy]-2-methylquinoline

HRID 1604598
Notes
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Reaction equation

HRID 1604598 reaction equation
[NH2:1][C:2]1[C:3]([Cl:22])=[C:4]([C:18]([Cl:21])=[CH:19][CH:20]=1)[CH2:5][O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([CH3:17])[CH:13]=[CH:12]2.[CH3:23][O:24][C:25]([CH2:27][CH2:28][C:29](Cl)=[O:30])=[O:26].C(=O)([O-])O.[Na+]>O.C(N(CC)CC)C.ClCCl>[Cl:22][C:3]1[C:2]([NH:1][C:29](=[O:30])[CH2:28][CH2:27][C:25]([O:24][CH3:23])=[O:26])=[CH:20][CH:19]=[C:18]([Cl:21])[C:4]=1[CH2:5][O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([CH3:17])[CH:13]=[CH:12]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl ester2×HCID 516892Sodium BicarbonateHCID 108065208-(3-Amino-2,6-dichlorobenzyloxy)-2-methylquinoline

Product 1

HCID 196032998-[2,6-Dichloro-3-(3-methoxycarbonylpropionylamino)benzyloxy]-2-methylquinoline

Reagents, catalysts & solvents 3

HCID 962Water
Solvent
HCID 6344DichloromethaneSolvent
HCID 8471TriethylamineSolvent2×

Procedure

To a mixture of 8-(3-amino-2,6-dichlorobenzyloxy)-2-methylquinoline (1.67 g), triethylamine (0.9 ml) and anhydrous dichloromethane (84 ml) was added 3-methoxycarbonylpropionyl chloride (0.7 ml). After stirring at ambient temperature for 9 hours, triethylamine (1.8 ml) and 3-methoxycarbonylpropionyl chloride (1.4 ml) were added thereto and the mixture was stirred for additional 30 minutes. The reaction mixture was washedwith water and saturated aqueous solution of sodium hydrogen carbonate, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a silica gel column chromatography eluted with chloroform to give 8-[2,6-dichloro-3-(3-methoxycarbonylpropionylamino)benzyloxy]-2-methylquinoline (2.04 g) as a pale yellow oil.

Workup

  1. stirringthe mixture was stirred for additional 30 minutes
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by a silica gel column chromatography
  5. washeluted with chloroform

Sources & evidence

ORD record
ord-3bc2f154716b48588c8f7a6a18d0dd58
Source dataset
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05994368

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes