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Diisopropylethylamine → Methyl 4-[(2-chloroquinoline-4-carbonyl)amino]-3,5-dimethyl-benzoate

HRID 239978
Notes
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Reaction equation

HRID 239978 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:25]([CH3:26])=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=1[CH3:27].C(N(CC)C(C)C)(C)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])=[CH:18][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:24][C:25]=2[CH3:26])=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 2305822-Chloroquinoline-4-carboxylic acidHCID 11030398Benzoic acid, 4-amino-3,5-dimethyl-, methyl ester

Product 1

HCID 86707363Methyl 4-[(2-chloroquinoline-4-carbonyl)amino]-3,5-dimethyl-benzoateYield 960.3%

Reagents, catalysts & solvents

2
HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-chloroquinoline-4-carboxylic acid (5.00 g, 0.0024 mol) in CH2Cl2 (50 mL) at 0° C. are added methyl 4-amino-3,5-dimethylbenzoate (3.88 g, 0.02167 mol, see preparation 12) and N,N-diisopropylethylamine (12.5 ml, 0.07225 mol). After stirring the reaction mixture for 10 minutes, 1-propanephosphonic acid cyclic anhydride (50% solution in ethyl acetate, 31.0 ml, 0.048 mol) is added via syringe and heated at 40° C. After 5 hours, the reaction mixture is diluted with water and extracted with dichloromethane. The organic layers are combined and dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (silica gel) using a gradient of 0-40% ethyl acetate in hexanes. After purification the solid is triturated with 20% diethyl ether in pentane and dried to give the title compound as a white solid (8.50 g, 96%). Mass spectrum (m/z): 369.1 (M+1).

Workup

  1. waitAfter 5 hours
  2. extractionextracted with dichloromethane
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by flash chromatography (silica gel)
  7. customAfter purification the solid
  8. customis triturated with 20% diethyl ether in pentane
  9. customdried

Sources & evidence

ORD record
ord-543cff2aef534d55add2ec8d683941a5
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08642768B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes