Propionic Acid → HCID 18322271, compound

HRID 1698862Notes

Reaction equation

HRID 1698862 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([C:10]([O:12][CH3:13])=[O:11])=[CH:6][C:4]=1[NH2:5].[BH4-].[Na+].[OH-].[Na+].[C:18](O)(=O)[CH2:19][CH3:20]>>[CH2:18]([NH:5][C:4]1[CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=[CH:9][C:3]=1[O:2][CH3:1])[CH2:19][CH3:20]

Participants

5

Reactant 4

HCID 1032Propionic AcidHCID 14798Sodium HydroxideHCID 2734814Methyl 3-Amino-4-methoxybenzoateHCID 4311764Sodium borohydride

Product 1

HCID 18322271HCID 18322271, compound

Procedure

15 g of 2-methoxy-5-methoxycarbonylaniline are dissolved in 500 ml of propionic acid under argon and at room temperature and 15.7 g of sodium borohydride are added in small portions. The reaction mixture is stirred for 2 hours and then hydrolyzed and alkalinized with 10 N sodium hydroxide while the temperature is maintained below 20° C. It is extracted with dichloromethane, the organic phase is washed with a saturated NaCl solution, dried and then evaporated under vacuum. The expected product is obtained in the form of an oil with a quantitative yield.

Workup

  1. temperatureis maintained below 20° C
  2. extractionIt is extracted with dichloromethane
  3. washthe organic phase is washed with a saturated NaCl solution
  4. customdried
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-b63b703cad144ee6b5f0088cfb155eb0
Source dataset
uspto-grants-2002_02
Patent number
US06344470B1

Reaction notes

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