Hydrochloric Acid → HCID 18694219, compound

HRID 1740752Notes

Reaction equation

HRID 1740752 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=2)=[C:4]([CH3:18])[CH:3]=1.C(N(CC)CC)C.[Cl:26][CH2:27][CH2:28][CH2:29][C:30](Cl)=[O:31].Cl>ClCCl.O>[Cl:26][CH2:27][CH2:28][CH2:29][C:30]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:13]=2)=[C:4]([CH3:18])[CH:3]=1)=[O:31]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 21948355Methyl 4'-amino-2'-methyl[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 18694219HCID 18694219, compoundYield 41.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 4'-amino-2'-methylbiphenyl-4-carboxylate (D27) (1.84 g, 7.6 mmol) and triethylamine (2.6 ml, 19 mmol) were stirred in dichloromethane (100 ml) as 4-chlorobutyryl chloride (0.94 ml, 8.4 mmol) was added dropwise. The mixture was stirred for 1 h, vigorously stirred with water for 15 min, acidified (5M HCl), and separated. The organic phase was washed with water and K2CO3 /brine solution, dried (Na2SO4) and evaporated to give a light yellow solid. Chromatography on silica gel, eluting with 0-40% ether/dichloromethane, gave the title compound (1.08 g, 41%) as a light yellow solid.

Workup

  1. additionwas added dropwise
  2. customseparated
  3. washThe organic phase was washed with water and K2CO3 /brine solution
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto give a light yellow solid
  7. washChromatography on silica gel, eluting with 0-40% ether/dichloromethane

Sources & evidence

ORD record
ord-b6bbaa5c3ee3451babd34f2069ea6fe6
Source dataset
uspto-grants-1999_10
Patent number
US05972935

Reaction notes

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