Butanoic acid, 2-ethyl-3-oxo-, ethyl ester → HCID 13066356, compound

HRID 1995316Notes

Reaction equation

HRID 1995316 reaction equation
[NH2:1][C:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]=1.[CH2:9]([CH:11]([C:17]([CH3:19])=O)[C:12](OCC)=[O:13])[CH3:10]>C(O)C>[CH2:17]([C:11]1[C:12](=[O:13])[N:8]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]2=[N:1][C:9]=1[CH3:10])[CH3:19]

Participants

4

Reactant 2

HCID 79065Butanoic acid, 2-ethyl-3-oxo-, ethyl esterHCID 97937283,4,5,6-tetrahydro-2H-azepin-7-amine

Product 1

HCID 13066356HCID 13066356, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.6 g. of 7-amino-3,4,5,6-tetrahydro-2H-azepine and 7.5 g. of ethyl 2-ethyl-acetoacetate are boiled in 50 ml. ethanol for 3 hours. The ethanol is then evaporated at reduced pressure. The residual oil is dissolved in 20 ml. of 10% hydrochloric acid and shaken out twice with 10 ml. ethyl acetate. The aqueous layer is neutralized with sodium hydrogen carbonate and shaken out with 3×10 ml. chloroform. The combined chloroform layer is dried over calcinated sodium sulphate and evaporated. The residual colorless oil is fractionated at reduced pressure. 6.3 g. (61%) 3-ethyl-2-methyl-4-oxo-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepine are obtained. Boiling point: 156°-160° C./2 mmHg.

Workup

  1. customThe ethanol is then evaporated at reduced pressure
  2. dissolutionThe residual oil is dissolved in 20 ml
  3. stirringshaken out with 3×10 ml
  4. dry with materialThe combined chloroform layer is dried
  5. customevaporated

Sources & evidence

ORD record
ord-e032e72cfc3347d4933cff4d8c179b18
Source dataset
uspto-grants-1983_09
Patent number
US04404205

Reaction notes

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