Formate → 3-Hydroxy-3-methylglutaric acid monoamide

HRID 1706592Notes

Reaction equation

HRID 1706592 reaction equation
O[CH:2]([CH2:7]C#N)[CH:3]([CH3:6])[C:4]#N.OO.Cl.[OH-:13].[NH4+:14].[CH:15]([O-:17])=[O:16].[OH2:18]>>[OH:13][C:3]([CH3:6])([CH2:4][C:15]([OH:17])=[O:16])[CH2:2][C:7]([NH2:14])=[O:18]

Participants

7

Reactant 6

HCID 283FormateHCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 962Water2×HCID 14923Ammonium HydroxideHCID 203336383-Hydroxy-methylglutaronitrile

Product 1

HCID 127207103-Hydroxy-3-methylglutaric acid monoamide

Procedure

A mixture of 20 g. (0.16 moles) of 3-hydroxy-methylglutaronitrile, 200 ml of water, 32 ml (0.33 moles) of 30% hydrogen peroxide and 70 ml of 12 N hydrochloric acid is stirred at 25° C. for approximately 3 hours and then heated at reflux for 30 minutes. Thereafter the mixture is cooled, diluted to 1 liter with water and the pH adjusted to 7 with 14 N ammonium hydroxide. The mixture is passed through a 250 ml column of Dowex 2 resin in the formate form and the column is then washed with 1 liter of water. Thereafter the product is eluted with 1 liter of 0.1 N formic acid and the eluate evaporated to dryness under vacuum to afford 3-hydroxy-3-methylglutaric acid monoamide.

Workup

  1. additionA mixture of 20 g
  2. temperatureheated
  3. temperatureat reflux for 30 minutes
  4. temperatureThereafter the mixture is cooled
  5. washthe column is then washed with 1 liter of water
  6. washThereafter the product is eluted with 1 liter of 0.1 N formic acid
  7. customthe eluate evaporated to dryness under vacuum

Sources & evidence

ORD record
ord-d13c7ae1a99f43a0b35b12fda987d42a
Source dataset
uspto-grants-1980_06
Patent number
US04208204

Reaction notes

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