Ammonia → HCID 178437742, compound

HRID 259811Notes

Reaction equation

HRID 259811 reaction equation
[NH3:1].[Cl:2][CH:3]([C:8](=O)[CH2:9][CH3:10])[C:4](OC)=[O:5].[CH:12]([NH2:14])=O>>[Cl:2][C:3]1[C:4]([OH:5])=[N:1][CH:12]=[N:14][C:8]=1[CH2:9][CH3:10]

Participants

4

Reactant 3

HCID 222Ammonia2×HCID 713FormamideHCID 545096Methyl 2-chloro-3-oxopentanoate

Product 1

HCID 178437742HCID 178437742, compound

Conditions

Temperature
50 °C

Procedure

NH3 gas is passed with cooling (max. 50° C.) through a solution of 99.7 g (0.6 mol) of methyl 2-chloro-3-oxo-valerate in 130 ml of formamide until the mixture takes up no more NH3 (about 1 h). The ammonia residues are removed by blowing out with nitrogen and applying a vacuum. The reaction solution is subsequently added dropwise to 450 ml of a 30% NaOMe solution in methanol at 50° C. Addition of a further 50 ml of formamide is followed by heating at 50° C. for 3 h. The volatile constituents are evaporated in vacuo, and subsequently the mixture is added to water and the pH is adjusted to 6 with HCl. Extraction with ethyl acetate and evaporation provide 91.2 g of crude product, which is recrystallized from cold acetone. Yield: 66.3 g (70%)

Workup

  1. customThe ammonia residues are removed
  2. additionThe reaction solution is subsequently added dropwise to 450 ml of a 30% NaOMe solution in methanol at 50° C
  3. additionAddition of a further 50 ml of formamide
  4. customThe volatile constituents are evaporated in vacuo
  5. additionsubsequently the mixture is added to water
  6. extractionExtraction
  7. customwith ethyl acetate and evaporation

Sources & evidence

ORD record
ord-0f6af429aefc48f38dfa518df37fbd09
Source dataset
uspto-grants-1996_06
Patent number
US05523404

Reaction notes

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