Hydrazine hydrate (1:1) → HCID 69960461, compound

HRID 1699210Notes

Reaction equation

HRID 1699210 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[C:25]([CH3:26])=[CH:24][CH:23]=[C:22](/[C:27](/[CH3:41])=[CH:28]\[CH2:29][N:30]2C(=O)C3=CC=CC=C3C2=O)[C:21]=1[CH3:42])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>C(O)C>[NH2:30][CH2:29]/[CH:28]=[C:27](\[C:22]1[C:21]([CH3:42])=[C:20]([CH2:19][O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:25]([CH3:26])=[CH:24][CH:23]=1)/[CH3:41]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 69960930HCID 69960930, compound

Product 1

HCID 69960461HCID 69960461, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 1-tert-butyldiphenylsilyloxymethyl-2,6-dimethyl-3-((Z)-1-methyl-3-phthalimido-1-propenyl)benzene (94 mg) in ethanol (1 ml) was added hydrazine monohydrate (16.4 mg), and the mixture was refluxed for 1 hour. After cooling, the insoluble material was filtered off, and the filtrate was concentrated in vacuo. To the residue was added dichloromethane, and the insoluble material was filtered off. The filtrate was concentrated in vacuo to give 3-((Z)-3-amino-1-methyl-1-propenyl)-1-tert-butyldiphenylsilyloxymethyl-2,6-dimethylbenzene (66 mg) as pale yellow amorphous.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperatureAfter cooling
  3. filtrationthe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. additionTo the residue was added dichloromethane
  6. filtrationthe insoluble material was filtered off
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b54cfd25b91c4957b1c5db9bc70fc8b7
Source dataset
uspto-grants-2002_02
Patent number
US06344462B1

Reaction notes

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