Hydrochloric Acid → HCID 14093060, compound

HRID 1381678Notes

Reaction equation

HRID 1381678 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[C:11]([CH:13]([CH2:18][CH:19](OC)OC)[C:14]([O:16][CH3:17])=[O:15])#[N:12].Cl>O1CCCC1>[C:11]([CH:13]([C:18]1[C:7]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:8]=2)[NH:9][CH:19]=1)[C:14]([O:16][CH3:17])=[O:15])#[N:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 77023(4-Methoxyphenyl)hydrazineHCID 14093058HCID 14093058, compound

Product 1

HCID 14093060HCID 14093060, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
67 °C

Procedure

A vigorously stirred suspension of para-methoxyphenylhydrazine chlorhidrate (6.47 g, 0.037 mole) in 260 ml of tetrahydrofuran was heated to 67° C. under an argon atmosphere. Compound IV, prepared above (10 g, 0.054 mole)was added at once and a solution of 12 ml of 10N hydrochloric acid in 70 ml of tetrahydrofuran was added over a period of 10 minutes. The reaction mixture was heated at reflux temperature for 35 minutes and further treated as described in Example 3. After chromatography on Silica gel 62 with hexane-ethyl acetate (3:1 v:v) solvent and evaporation of the solvent in vacuo, the viscous oily residue was crystallized from chloroform-hexane to yield 3.65 g (40.3%) of product mp 98°-100° C.

Workup

  1. additionwas added over a period of 10 minutes
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux temperature for 35 minutes
  4. additionfurther treated
  5. customAfter chromatography on Silica gel 62 with hexane-ethyl acetate (3:1 v:v) solvent and evaporation of the solvent in vacuo
  6. customthe viscous oily residue was crystallized from chloroform-hexane

Sources & evidence

ORD record
ord-31fc4518d157485681f3e78218c4d352
Source dataset
uspto-grants-1989_02
Patent number
US04803284

Reaction notes

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