Ammonium Hydroxide → HCID 54497968, compound

HRID 361601Notes

Reaction equation

HRID 361601 reaction equation
[CH2:1]([NH:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)=O)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[NH4+]>O>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:10]1[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2][CH2:1][N:9]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 2450326HCID 2450326, compound

Product 1

HCID 54497968HCID 54497968, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
155 °C

Procedure

A mixture of 14 g of pyridine-2-carboxylic acid phenethyl-amide and 300 g of polyphosphoric acid was stirred at 140° C. for 90 min., at 150° C. for 60 min. and finally at 155° C. for 60 min. The solution was cooled to 120° C. and poured into 2 l of water while stirring. The mixture was stirred at room temperature for a further 15 min. and made basic (strong warming|) by the addition of about 300 ml of 25% ammonium hydroxide while cooling with ice and stirring. Thereafter, the mixture was extracted with 2×400 ml of ethyl acetate. The combined raspberry-red organic phases were washed with 100 ml of 10% sodium chloride solution, dried over sodium sulfate, treated with about 5 g of Darco G60 and evaporated to dryness. There were obtained 11.6 g of 1-pyridin-2-yl-3,4-dihydro-isoquinoline as a yellowish oil, b.p. 130° C./0.08 mbar (bulb-tube).

Workup

  1. temperatureThe solution was cooled to 120° C.
  2. stirringwhile stirring
  3. stirringThe mixture was stirred at room temperature for a further 15 min.
  4. temperaturewhile cooling with ice
  5. stirringstirring
  6. extractionThereafter, the mixture was extracted with 2×400 ml of ethyl acetate
  7. washThe combined raspberry-red organic phases were washed with 100 ml of 10% sodium chloride solution
  8. dry with materialdried over sodium sulfate
  9. additiontreated with about 5 g of Darco
  10. customand evaporated to dryness

Sources & evidence

ORD record
ord-058200961a3145db91c231df5cc66b28
Source dataset
uspto-grants-1999_02
Patent number
US05866583

Reaction notes

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