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Triethylamine → Methyl 3-[(2-chloroquinoline-4-carbonyl)amino]-2,4-dimethyl-benzoate

HRID 239982
Notes
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Reaction equation

HRID 239982 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12]([OH:14])=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:15][C:16]1[C:17]([CH3:27])=[C:18]([CH:23]=[CH:24][C:25]=1[CH3:26])[C:19]([O:21][CH3:22])=[O:20].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>C(Cl)Cl.O>[Cl:1][C:2]1[CH:11]=[C:10]([C:12]([NH:15][C:16]2[C:17]([CH3:27])=[C:18]([CH:23]=[CH:24][C:25]=2[CH3:26])[C:19]([O:21][CH3:22])=[O:20])=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 2305822-Chloroquinoline-4-carboxylic acidHCID 66871802Methyl 3-amino-2,4-dimethylbenzoate

Product 1

HCID 86707367Methyl 3-[(2-chloroquinoline-4-carbonyl)amino]-2,4-dimethyl-benzoateYield 87.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloroquinoline-4-carboxylic acid (0.40 g, 0.0019 mol) in CH2Cl2 (8 mL) at 0° C. are added methyl 3-amino-2,4-dimethylbenzoate (0.31 g, 0.0017 mol, see preparation 10) and triethylamine (0.80 ml, 0.0058 mol). After stirring the reaction mixture for 10 minutes, 1-propanephosphonic acid cyclic anhydride (50% solution in ethyl acetate, 2.45 ml, 0.0038 mol) is added via syringe and stirred at room temperature. After 16 hours, the reaction is diluted with water and extracted twice with dichloromethane. The organic layers are combined and dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue is triturated with 20% diethyl ether in pentane and filtered to give the title compound as an off-white solid (0.55 g, 77%). Mass spectrum (m/z): 369.1 (M+1).

Workup

  1. stirringstirred at room temperature
  2. waitAfter 16 hours
  3. extractionextracted twice with dichloromethane
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue is triturated with 20% diethyl ether in pentane
  8. filtrationfiltered

Sources & evidence

ORD record
ord-6f0ea8d061d54ba3b40e3ef34ccef83c
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08642768B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes