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Triethylamine → Methyl 3-[(3-bromonaphthalene-1-carbonyl)amino]-2,4-dimethyl-benzoate

HRID 1427137
Notes
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Reaction equation

HRID 1427137 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]([OH:14])=O)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[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>[Br:1][C:2]1[CH:3]=[C:4]([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:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 117086093-Bromonaphthalene-1-carboxylic acidHCID 66871802Methyl 3-amino-2,4-dimethylbenzoate

Product 1

HCID 86707371Methyl 3-[(3-bromonaphthalene-1-carbonyl)amino]-2,4-dimethyl-benzoateYield 88.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-1-naphthoic acid (0.40 g, 1.59 mmol) in CH2Cl2 (8 mL) at 0° C. are added methyl 3-amino-2,4-dimethylbenzoate (0.26 g, 1.43 mmol, see preparation 10) and triethylamine (0.78 ml, 5.38 mmol). After stirring the reaction mixture for 10 minutes, 1-propanephosphonic acid cyclic anhydride (50% solution in ethyl acetate, 2.03 ml, 3.18 mmol) is added via syringe and stirred at room temperature. After 16 hours, the reaction is diluted with water and extracted with ethyl acetate. 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) with 5% EtOAc in hexane as eluent to afford the product as a white solid (0.52 g, 79%). Mass spectrum (m/z): 412.3 (M+1).

Workup

  1. stirringstirred at room temperature
  2. waitAfter 16 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue is purified by flash chromatography (silica gel) with 5% EtOAc in hexane as eluent

Sources & evidence

ORD record
ord-10c481b6e0e14ca7872892143fb87539
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08933098B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes