Ammonia → Onychine

HRID 1683146Notes

Reaction equation

HRID 1683146 reaction equation
[C:1]1([C:7]2[N:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:8]=2[C:9]([O:11]CC)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N>C(OCC)C>[CH3:18][C:14]1[CH:15]=[CH:16][N:17]=[C:7]2[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=3[C:9](=[O:11])[C:8]=12

Participants

4

Reactant 2

HCID 222AmmoniaHCID 11064550HCID 11064550, compound

Product 1

HCID 72584Onychine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 51 g (0.211 mol) of ethyl 2-phenyl-4-methylnicotinate and 500 g of polyphosphoric acid was stirred at 140° C. for 7 hours, cooled, stirred into 700 g of ice, rendered alkaline with conc. ammonia solution and extracted with ethyl acetate. The combined extracts were washed twice with water, dried over K2CO3 and concentrated. The product thus obtained was then digested with diethyl ether for 2 hours, filtered off with suction and dried. Yield 18.6 g (45% of theory), yellowish crystals of m.p. 137°-139° C.

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed twice with water
  4. dry with materialdried over K2CO3
  5. concentrationconcentrated
  6. customThe product thus obtained
  7. filtrationfiltered off with suction
  8. customdried

Sources & evidence

ORD record
ord-4adfd238e74f4a349c48be3fe13e9e68
Source dataset
uspto-grants-1997_06
Patent number
US05637554

Reaction notes

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