Ammonium → HCID 178420706, compound

HRID 2351875Notes

Reaction equation

HRID 2351875 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17].[N-:21]=[N+:22]=[N-:23].[Na+].[Cl-].[NH4+].[NH4+].Cl>CN(C)C=O.CO>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([C:16]2[NH:23][N:22]=[N:21][N:17]=2)[CH:18]=[CH:19][CH:20]=1

Participants

8

Reactant 5

HCID 223AmmoniumHCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium Azide2×HCID 14501705HCID 14501705, compound

Product 1

HCID 178420706HCID 178420706, compoundYield 48.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 8.8 g of 3-(2-quinolylmethyloxy)benzonitrile, 2.3 g of sodium azide and 1.9 g of ammonium chloride in 100 ml of dimethylformamide is stirred at 140° C. for 7 hours. An additional amount of sodium azide (1.2 g) and ammonium (1.0 g) is added and stirring resumed at 140° C. for 17 hours. The mixture is poured over ice and acidified with hydrochloric acid. The crude product solidifies and is filtered off to give 11 g of crude product. The crude product is slurried with hot methanol and filtered off. To a hot solution of this material is added enough water to cause trubidity. On cooling the compound crystallizes and is filtered off to yield 5.0 g of pure material having a M.P. of 200°-205° C. dec.

Workup

  1. stirringstirring
  2. waitresumed at 140° C. for 17 hours
  3. additionThe mixture is poured over ice
  4. filtrationis filtered off
  5. customto give 11 g of crude product
  6. filtrationfiltered off
  7. additionTo a hot solution of this material is added enough water
  8. temperatureOn cooling the compound
  9. customcrystallizes
  10. filtrationis filtered off

Sources & evidence

ORD record
ord-d6ad8b0b8c4b475ea5a0bdce010372e7
Source dataset
uspto-grants-1989_10
Patent number
US04874769

Reaction notes

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