Methyl acetoacetate → HCID 10352731, compound

HRID 1008746Notes

Reaction equation

HRID 1008746 reaction equation
Cl.[NH:2]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[C:6]#[N:7])[NH2:3].[C:12](OC)(=[O:17])[CH2:13][C:14]([CH3:16])=O.[Na].CO.C[O-].[Na+]>CO>[C:6]([C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N:2]1[C:12](=[O:17])[CH:13]=[C:14]([CH3:16])[NH:3]1)#[N:7]

Participants

6

Reactant 4

HCID 7757Methyl acetoacetateHCID 10942334Sodium MethoxideHCID 44717141HCID 44717141, compoundHCID 86653488Methanol sodium

Product 1

HCID 10352731HCID 10352731, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8.5 g (0.05 mol) of 2-hydrazino benzonitrile hydrochloride, 6 g (0.05 mol) of methyl acetoacetate and 100 ml of methanol were added into a 250 ml reaction flask, and then 50% methanol sodium solution (5.5 g (0.051 mol) sodium methoxide dissolved in 50 ml methanol) was added under stirring. After stirring for 10 min, the mixture was heated and refluxed for 6 h, and immediately filtered. The solid was washed with 20 ml of methanol. The methanol was recovered until the remained volume was 50 ml. 200 ml of ice water was poured with stirring to give the solid. The solid was filtered and washed with water to give 7 g of light yellow solid.

Workup

  1. stirringAfter stirring for 10 min
  2. temperaturethe mixture was heated
  3. temperaturerefluxed for 6 h
  4. filtrationimmediately filtered
  5. washThe solid was washed with 20 ml of methanol
  6. customThe methanol was recovered until the remained volume
  7. addition200 ml of ice water was poured
  8. stirringwith stirring
  9. customto give the solid
  10. filtrationThe solid was filtered
  11. washwashed with water

Sources & evidence

ORD record
ord-04bcc27f5bf042dc9157d034a50db635
Source dataset
uspto-grants-2011_07
Patent number
US07973036B2

Reaction notes

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