Triethylamine → Methyl 3-pentanamidobenzoate

HRID 1655458Notes

Reaction equation

HRID 1655458 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(N(CC)CC)C.[C:19](Cl)(=[O:24])[CH2:20][CH2:21][CH2:22][CH3:23]>C(Cl)Cl>[C:19]([NH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])(=[O:24])[CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 78274Benzoic acid, 3-amino-, methyl ester

Product 1

HCID 19171455Methyl 3-pentanamidobenzoateYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-aminobenzoate (6.0 g) and triethylamine (4.5 g) in methylene chloride (90 ml) was added dropwise, while stirring under ice-cooling, valeryl chloride (4.8 g). The mixture was stirred for one hour. The reaction mixture was washed with an aqueous solution of sodium bicarbonate, dilute hydrochloric acid and water, followed by drying and concentration to dryness. The concentrate was crystallized from ethyl acetate-hexane to afford colorless prisms (8.1 g, 87%), m.p. 101-102° C. 1H-NMR(90 MHz, CDCl3) δ: 0.93(3H,t), 1.2-1.9(4H,m), 2.37(2H,t), 3.90(3H,s), 7.36(1H,t), 7.5(1H,br s), 7.70-7.95(2H,m), 8.03(1H,t).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for one hour
  3. washThe reaction mixture was washed with an aqueous solution of sodium bicarbonate, dilute hydrochloric acid and water
  4. customby drying
  5. concentrationconcentration to dryness
  6. customThe concentrate was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-91fe659132c044d79ba4709a086d533d
Source dataset
uspto-grants-1993_10
Patent number
US05250554

Reaction notes

Loading…