Hydrazine hydrate (1:1) → HCID 178452683, compound

HRID 1276253Notes

Reaction equation

HRID 1276253 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=O)[CH:15]=[CH:16][N:17](C)C)=[C:10]([Cl:21])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].O.[NH2:24]N>C(O)C.C(OCC)C>[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][NH:17][N:24]=2)=[C:10]([Cl:21])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 54077142HCID 54077142, compound

Product 1

HCID 178452683HCID 178452683, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of [3-chloro-4-(3-dimethylamino-acryloyl)-phenyl]-carbamic acid tert-butyl ester (250 mg) in ethanol (1.25 ml) is treated with hydrazine hydrate (0.2:5 ml) and the mixture is stirred at room temperature for 3 hours. The mixture is then diluted with 30 mL of diethyl ether, washed three times with water, once with saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent is removed by evaporation under reduced pressure and the resulting residue is chromatographed over silica gel (67% ethyl acetate in hexanes is used as the eluant) to provide the desired product as an oil.

Workup

  1. washwashed three times with water
  2. dry with materialonce with saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate
  3. customThe solvent is removed by evaporation under reduced pressure
  4. customthe resulting residue is chromatographed over silica gel (67% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-3a6b32622c9a4fce9c6f5aa1a580802c
Source dataset
uspto-grants-2000_12
Patent number
US06166028

Reaction notes

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