4-Chlorobenzoyl chloride → HCID 43623645, compound

HRID 1818920Notes

Reaction equation

HRID 1818920 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C[Si](C=[N+]=[N-])(C)C.[Cl:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1.[CH3:29]CN(C(C)C)C(C)C>CO.C1(C)C=CC=CC=1>[CH3:29][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([CH3:11])[CH:9]=[CH:10][C:2]=1[NH:1][C:24](=[O:25])[C:23]1[CH:27]=[CH:28][C:20]([Cl:19])=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 85014-Chlorobenzoyl chlorideHCID 762552-Amino-5-methylbenzoic acidHCID 81531DiisopropylethylamineHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 43623645HCID 43623645, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 2-amino-5-methyl benzoic acid (1.0 mmol) dissolved in 10% MeOH in toluene (2.5 mL) is added dropwise trimethylsilyl-diazomethane (2.0 M in hexanes, 0.75 mL). The reaction mixture is stirred at room temperature for 1 hour and the solvent is removed under reduced pressure. The resulting methyl ester is dissolved in dichloromethane (3.0 mL) and then 4-chlorobenzoyl chloride (1.0 equivalent) and DIEA (1.0 equivalent) is added sequentially. The reaction mixture is stirred for 3 hours and the solvent is evaporated. The yellow residue is diluted with EtOAc, washed with 1 M NaHSO4, brine, dried, filtered and concentrated under reduced pressure to provide 2-(4-chloro-benzoylamino)-5-methyl-benzoic acid methyl ester (compound 11.1) which is used without purification in the next step.

Workup

  1. customthe solvent is removed under reduced pressure
  2. dissolutionThe resulting methyl ester is dissolved in dichloromethane (3.0 mL)
  3. stirringThe reaction mixture is stirred for 3 hours
  4. customthe solvent is evaporated
  5. additionThe yellow residue is diluted with EtOAc
  6. washwashed with 1 M NaHSO4, brine
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e7a0b050c30c4a62a4e1478d99a5f8b0
Source dataset
uspto-grants-2009_10
Patent number
US07601725B2

Reaction notes

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