Water → HCID 59255932, compound

HRID 222605Notes

Reaction equation

HRID 222605 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Cl:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=1[NH:22][NH2:23])[C:15](OC)=[O:16].O>C1(C)C=CC=CC=1>[Cl:11][C:12]1[CH:13]=[C:14]([CH2:15][OH:16])[CH:19]=[CH:20][C:21]=1[NH:22][NH2:23]

Participants

5

Reactant 3

HCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 57417107HCID 57417107, compound

Product 1

HCID 59255932HCID 59255932, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-73 °C

Procedure

Diisobutylaluminium hydride (1M in toluene, 190 ml) is added dropwise, under a nitrogen atmosphere and at −73° C., to a solution of methyl 3-chloro-4-hydrazino-benzoate (9.5 g, 47 mmol) in 1 l of toluene in such a way that the temperature does not rise above −70° C. The reaction mixture is stirred at −73° C. for 30 min and then warmed to −5° C. Following hydrolysis with 500 ml of water, the precipitate is filtered off and washed with ethyl acetate (5×500 ml). The organic phase is evaporated, after which the residue is taken up in a little ethyl acetate and precipitated with petroleum ether/diethyl ether and filtered off. The solid which is obtained in this way is purified chromatographically on silica gel using cyclohexane/ethyl acetate. Yield: 2.9 g

Workup

  1. customdoes not rise above −70° C
  2. temperaturewarmed to −5° C
  3. filtrationthe precipitate is filtered off
  4. washwashed with ethyl acetate (5×500 ml)
  5. customThe organic phase is evaporated
  6. customprecipitated with petroleum ether/diethyl ether
  7. filtrationfiltered off
  8. customThe solid which is obtained in this way
  9. customis purified chromatographically on silica gel

Sources & evidence

ORD record
ord-8df4633103754c958c1b4e589fb6a854
Source dataset
uspto-grants-2012_06
Patent number
US08207349B2

Reaction notes

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