Hydrazine hydrate (1:1) → HCID 14011677, compound

HRID 845256Notes

Reaction equation

HRID 845256 reaction equation
O.NN.[CH3:4][C:5]1[NH:6][C:7]([CH3:40])=[C:8]([C:24]([O:26][CH2:27][CH2:28][N:29]2C(=O)C3=CC=CC=C3C2=O)=[O:25])[CH:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-:23])=[O:22])[C:10]=1[C:11]([O:13][CH3:14])=[O:12]>C(O)C>[CH3:4][C:5]1[NH:6][C:7]([CH3:40])=[C:8]([C:24]([O:26][CH2:27][CH2:28][NH2:29])=[O:25])[CH:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-:23])=[O:22])[C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 14011671HCID 14011671, compound

Product 1

HCID 14011677HCID 14011677, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1.5 ml (30 mmol) of hydrazine hydrate in 7.5 ml of ethanol are added dropwise to a boiling solution of 5.05 g (10 mmol) of 1,4-dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(2-nitrophenyl)-5-(2-phthalimidoethoxy)carbonylpyridine in 50 ml of ethanol. Boiling is continued for 2 hours and the reaction mixture is then cooled and concentrated by evaporation under vacuum. The residue is stirred up with 25 ml of 2N-hydrochloric acid for 30 minutes at room temperature and the precipitated solid is removed by suction filtration and the filtrate is adjusted to pH 10 with conc. ammonia. The product is extracted three times with 30 ml portions of methylene chloride and the organic phases obtained are then dried and concentrated by evaporation. 2.91 g (77%) of a yellow amorphous solid is obtained as residue which is used without further purification.

Workup

  1. temperaturethe reaction mixture is then cooled
  2. concentrationconcentrated by evaporation under vacuum
  3. customthe precipitated solid is removed by suction filtration
  4. extractionThe product is extracted three times with 30 ml portions of methylene chloride
  5. customthe organic phases obtained
  6. customare then dried
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-327caf95b8c748eb93a98f6b6663caa0
Source dataset
uspto-grants-1988_07
Patent number
US04757080

Reaction notes

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