Acetic Anhydride → Methyl 4-acetamido-6-chloro-4'-(dimethylamino)-[1,1'-biphenyl]-3-carboxylate

HRID 2174549Notes

Reaction equation

HRID 2174549 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]2[CH:14]=[CH:13][C:12]([N:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:18]([O:20][CH3:21])=[O:19].[C:22](OC(=O)C)(=[O:24])[CH3:23]>>[C:22]([NH:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]2[CH:10]=[CH:11][C:12]([N:15]([CH3:16])[CH3:17])=[CH:13][CH:14]=2)=[CH:4][C:3]=1[C:18]([O:20][CH3:21])=[O:19])(=[O:24])[CH3:23]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 68352236HCID 68352236, compound2×

Product 1

HCID 68352041Methyl 4-acetamido-6-chloro-4'-(dimethylamino)-[1,1'-biphenyl]-3-carboxylateYield 90.1%

Procedure

Methyl 4-amino-6-chloro-4′-(dimethylamino)-[1,1′-biphenyl]-3-carboxylate (Intermediate 47) (2 g, 6.56 mmol) was dissolved in acetic anhydride (Aldrich, 6.75 mL, 92 mmol) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into ice water and the resulting precipitate was isolated by filtration and dried. The solid was triturated with methanol, filtered and dried to give the title compound methyl 4-acetamido-6-chloro-4′-(dimethylamino)-[1,1′-biphenyl]-3-carboxylate (2.05 g, 5.91 mmol, 90% yield) as beige solid. LCMS: (M+H)+=347; Rt=3.76 min.

Workup

  1. customthe resulting precipitate was isolated by filtration
  2. customdried
  3. customThe solid was triturated with methanol
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-a8769168855341208f84bfa60d07191f
Source dataset
uspto-grants-2015_06
Patent number
US09061998B2

Reaction notes

Loading…