HCID 13355660, compound → HCID 13355752, compound

HRID 1111967Notes

Reaction equation

HRID 1111967 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([CH:10]([OH:16])[CH2:11][NH:12][CH:13]2[CH2:15][CH2:14]2)=[CH:4][C:3]=1Br.[H][H]>CO>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH:10]([OH:16])[CH2:11][NH:12][CH:13]2[CH2:15][CH2:14]2)=[CH:6][C:7]=1[C:8]#[N:9]

Participants

4

Reactant 2

HCID 13355660HCID 13355660, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13355752HCID 13355752, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4 gm of 1-(4'-amino-3'-bromo-5'-cyano-phenyl)-2-cyclopropylamino-ethanol was dissolved in methanol, and the solution was hydrogenated at room temperature at a hydrogen pressure of 3 to 5 atmospheres after addition of 1 gm of palladized coal (10%). After termination of hydrogen absorption, the catalyst was suction-filtered off, the filtrate was evaporated to dryness in vacuo, and the residue was distributed between dilute sodium hydroxide and chloroform. After evaporation of the chloroform phase, 1-(4'-amino-3'-cyano-phenyl)-2-cyclopropylamino-ethanol was obtained as an oil, which was purified chromatographically on silicagel (eluant: chloroform:methanol = 9:1). The dihydrochloride, obtained by addition of ethereal hydrochloric acid, was recrystallized from isopropanol. M.p. 148°-151° C. (decomp.).

Workup

  1. additionafter addition of 1 gm of palladized coal (10%)
  2. customAfter termination of hydrogen absorption
  3. filtrationthe catalyst was suction-filtered off
  4. customthe filtrate was evaporated to dryness in vacuo
  5. customAfter evaporation of the chloroform phase

Sources & evidence

ORD record
ord-bfe105b527cd44cf8905084057c430f1
Source dataset
uspto-grants-1978_10
Patent number
US04119710

Reaction notes

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