Diboron → HCID 436319, compound

HRID 2286348Notes

Reaction equation

HRID 2286348 reaction equation
[CH3:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[CH2:12][C:13]#[N:14].B#B>O1CCCC1>[CH3:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][NH2:14]

Participants

4

Reactant 2

HCID 6328200DiboronHCID 136975832-(3,4-Dimethoxy-2-methylphenyl)acetonitrile

Product 1

HCID 436319HCID 436319, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 42 g (0.219 m) of the phenylacetonitrile 100 ml of tetrahydrofuran was mixed with 400 ml of 1 molar diborane in tetrahydrofuran then heated at reflux for 21/2 hours. After cooling the mixture was quenched with 150 ml of methanol. After sitting overnight, the mixture was stripped. An excess of 10% hydrochloric acid was added followed by heating on the steambath for 2 hours. After cooling, ether was added. The mixture was stirred for 1/2 hour and evaporated. The remaining aqueous layer was made basic with 10% sodium hydroxide, extracted with ether which was dried and evaporated to give 2-methyl-3,4-dimethoxyphenethylamine.

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 21/2 hours
  3. temperatureAfter cooling the mixture
  4. customwas quenched with 150 ml of methanol
  5. additionAn excess of 10% hydrochloric acid was added
  6. temperatureby heating on the steambath for 2 hours
  7. temperatureAfter cooling
  8. additionether was added
  9. customevaporated
  10. extractionextracted with ether which
  11. customwas dried
  12. customevaporated

Sources & evidence

ORD record
ord-5643b65ee3514eccaa211517a8a859dc
Source dataset
uspto-grants-1981_05
Patent number
US04265889

Reaction notes

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