Dichloromethane → 5-Isobutyrylamino-4'-methyl-biphenyl-3-carboxylic acid methyl ester

HRID 340621Notes

Reaction equation

HRID 340621 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:8]=[C:9]([NH2:11])[CH:10]=1)=[O:4].C(N(CC)CC)C.ClCCl.[C:29](Cl)(=[O:33])[CH:30]([CH3:32])[CH3:31]>O.Cl>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:8]=[C:9]([NH:11][C:29](=[O:33])[CH:30]([CH3:32])[CH3:31])[CH:10]=1)=[O:4]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 57850917Methyl 5-amino-4'-methylbiphenyl-3-carboxylate

Product 1

HCID 596275325-Isobutyrylamino-4'-methyl-biphenyl-3-carboxylic acid methyl esterYield 101.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

5-Amino-4′-methyl-biphenyl-3-carboxylic acid methyl ester (0.10 g, 2.49 mmol) and triethylamine (6.75 g, 7.47 mmol) were added to dichloromethane (40 mL) and stirred under nitrogen atmosphere. Isobutyryl chloride (0.318 g, 2.98 mmol) was added slowly, and the reaction mixture was stirred for 2.5 hours at room temperature. The mixture was diluted with water and 1N aqueous HCl, and the organic layer was separated, washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure to give 0.786 g of 5-isobutyrylamino-4′-methyl-biphenyl-3-carboxylic acid methyl ester.

Workup

  1. stirringthe reaction mixture was stirred for 2.5 hours at room temperature
  2. customthe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4e119243434a453c9fe99f82faccd0a1
Source dataset
uspto-grants-2014_11
Patent number
US08895589B2

Reaction notes

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