Ammonia → HCID 70456999, compound

HRID 1981852Notes

Reaction equation

HRID 1981852 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, 10.4 mM) cuprous cyanide (1.07 g, 5.4 mM), 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-bd91fa1cb6744e4084d7ac1da54b2cb5
Source dataset
uspto-grants-1986_06
Patent number
US04594195

Reaction notes

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