Methanol → HCID 19087793, compound

HRID 1464387Notes

Reaction equation

HRID 1464387 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1)([O-])=O.CO.O.NN>O1CCCC1.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 19087805HCID 19087805, compound

Product 1

HCID 19087793HCID 19087793, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

15 g (0.043 mol) of the compound from Example XXVIII are dissolved in 100 ml of tetrahydrofuran and 100 ml of methanol and 4 g (0.08 mol) of hydrazine monohydrate are added. Raney nickel is added in portions under argon with stirring, the temperature rising to 50° C. After the evolution of gas has ended, the mixture is heated to boiling for a further hour and then filtered while hot. The filtrate is concentrated in vacuo and the residual oil is taken up using 250 ml of dichloromethane. After washing twice using water and drying with sodium sulphate, the solvent is evaporated in vacuo and a colourless oil is obtained which crystallises overnight.

Workup

  1. customrising to 50° C
  2. temperaturethe mixture is heated
  3. waitto boiling for a further hour
  4. filtrationfiltered while hot
  5. concentrationThe filtrate is concentrated in vacuo
  6. washAfter washing twice using water
  7. dry with materialdrying with sodium sulphate
  8. customthe solvent is evaporated in vacuo
  9. customa colourless oil is obtained which
  10. customcrystallises overnight

Sources & evidence

ORD record
ord-a99f5e47a2e14313a9bd924b8bb49c8e
Source dataset
uspto-grants-1994_04
Patent number
US05304563

Reaction notes

Loading…