Triethylamine → Methyl 5-methyl-2-valerylaminobenzoate

HRID 1655462Notes

Reaction equation

HRID 1655462 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-ff028d6261134b78bbb83ff0aa09a48f
Source dataset
uspto-grants-1993_10
Patent number
US05250554

Reaction notes

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