Water → HCID 67820811, compound

HRID 1492510Notes

Reaction equation

HRID 1492510 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=O.[NH2:14][CH2:15][C:16]([N:18]([CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:17].O>ClCCl>[C:19]1([N:18]([CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:16](=[O:17])[CH2:15][NH:14][C:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)=[O:13])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7124Quinaldic AcidHCID 18951114HCID 18951114, compound

Product 1

HCID 67820811HCID 67820811, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 0.85 g of N,N'-carbonyldiimidazole in 10 cm3 of anhydrous dichloromethane is added dropwise, at a temperature close to 20° C., to a solution of 0.87 g of 2-quinolinecarboxylic acid in 15 cm3 of anhydrous dichloromethane. The suspension obtained is stirred for 3 hours at a temperature close to 20° C. and a solution of 2.6 g of tert-butyl 2-(2-amino-N-phenylacetamido)acetate in 25 cm3 of anhydrous dichloromethane is then added. The reaction mixture is stirred for 16 hours at a temperature close to 20° C. and 50 cm3 of water are then added. The aqueous phase is separated off by decanting and then reextracted with twice 15 cm3 of 1,2-dichloroethane. The organic phases are combined, washed with twice 25 cm3 of a saturated aqueous sodium bicarbonate solution and then with twice 25 cm3 of distilled water, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization of the residual solid from a mixture of cyclohexane and ethyl acetate (90/10 by volume), 0.8 g of tert-butyl 2-(N-phenyl-2-quinolinecarboxamidoacetamido)acetate melting at 114° C. is obtained.

Workup

  1. customThe suspension obtained
  2. customclose to 20° C.
  3. stirringThe reaction mixture is stirred for 16 hours at a temperature
  4. customclose to 20° C.
  5. customThe aqueous phase is separated off
  6. customby decanting
  7. washwashed with twice 25 cm3 of a saturated aqueous sodium bicarbonate solution
  8. dry with materialwith twice 25 cm3 of distilled water, dried over magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  11. customAfter recrystallization of the residual solid
  12. additionfrom a mixture of cyclohexane and ethyl acetate (90/10 by volume)

Sources & evidence

ORD record
ord-ff9a3bcb56ea47ad9403e0e826e20a5b
Source dataset
uspto-grants-1994_12
Patent number
US05374656

Reaction notes

Loading…