Ammonia → HCID 70456999, compound

HRID 1719198Notes

Reaction equation

HRID 1719198 reaction equation
Br[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([O:12][CH3:13])=[CH:4][CH:3]=1.[N:14]1C=CC=C[CH:15]=1.N>CN(C)P(N(C)C)(N(C)C)=O>[CH3:13][O:12][C:5]1([C:15]#[N:14])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:2]=[CH:3][CH2:4]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 1049PyridineHCID 22278773HCID 22278773, compound

Product 1

HCID 70456999HCID 70456999, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

4-Bromo-1-methoxy-5,6,7,8-tetrahydronaphthalene (1) (2.5 g, 10.4mM) cuprous cyanide (1.07 g, 5.4mM), pyridine (1.5 ml) and hexamethylphosphoramide (0.3 ml) were stirred at 192° C. for 16 hours. The mixture was poured into aqueous ammonia and extracted with ether. The ether was washed with ammonia, water, dilute hydrochloric acid and then saturated brine. The ether solution was then dried and evaporated to give the nitrile (2) (1.90 g).

Workup

  1. extractionextracted with ether
  2. washThe ether was washed with ammonia, water, dilute hydrochloric acid
  3. dry with materialThe ether solution was then dried
  4. customevaporated

Sources & evidence

ORD record
ord-031b4d019bd44147aa3efb1e532fae84
Source dataset
uspto-grants-1985_09
Patent number
US04539319

Reaction notes

Loading…