Triethylamine → Methyl 5-methyl-2-valerylaminobenzoate

HRID 653706Notes

Reaction equation

HRID 653706 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.[C:20](Cl)(=[O:25])[CH2:21][CH2:22][CH2:23][CH3:24]>C(Cl)Cl>[CH3:12][C:9]1[CH:10]=[CH:11][C:2]([NH:1][C:20](=[O:25])[CH2:21][CH2:22][CH2:23][CH3:24])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 1201104Methyl 2-Amino-5-methylbenzoate

Product 1

HCID 19792094Methyl 5-methyl-2-valerylaminobenzoateYield 104.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-amino-5-methylbenzoate (8.1 g) and triethylamine (6.0 g) in methylene chloride (50 ml) was added dropwise, while stirring under ice-cooling, valeryl chloride (6.5 g). The reaction was allowed to stir for two hours, then the reaction mixture was washed with an aqueous solution of sodium carbonate, dilute hydrochloric acid and water, followed by drying. The solvent was evaporated to dryness to give a pale brown oil (12.8 g, 99%).

Workup

  1. temperaturecooling
  2. stirringto stir for two hours
  3. washthe reaction mixture was washed with an aqueous solution of sodium carbonate, dilute hydrochloric acid and water
  4. customby drying
  5. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-7352affd105141e995fc2529a0f1e185
Source dataset
uspto-grants-1992_07
Patent number
US05128356

Reaction notes

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