Ammonium Chloride → HCID 178515577, compound

HRID 2092355Notes

Reaction equation

HRID 2092355 reaction equation
[O:1]=[C:2]1[CH2:11][CH:10]([C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=2)[C:15]#[N:16])[C:9]2[C:4](=[C:5]3[CH:23]=[CH:22][CH:21]=[CH:20][C:6]3=[CH:7][CH:8]=2)[NH:3]1.[N-:24]=[N+:25]=[N-:26].[Na+].[Cl-].[NH4+]>CN(C)C=O>[NH:24]1[C:15]([C:14]2[CH:13]=[C:12]([CH:10]3[C:9]4[C:4](=[C:5]5[CH:23]=[CH:22][CH:21]=[CH:20][C:6]5=[CH:7][CH:8]=4)[NH:3][C:2](=[O:1])[CH2:11]3)[CH:19]=[CH:18][CH:17]=2)=[N:16][N:26]=[N:25]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 59140321HCID 59140321, compound

Product 1

HCID 178515577HCID 178515577, compoundYield 39.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 3-(2-Oxo-1,2,3,4-tetrahydro-benzo[h]quinolin-4-yl)-benzonitrile (0.50 g, 1.68 mmol), sodium azide (0.13 g, 2.0 mmol) and ammonium chloride (0.11 g, 2.01 mmol) in dimethylformamide (3.5 ml) was heated with stirring at 130° C. for 18 hr. The solvent was removed in vacuo and water was added. The solution was acidified with dilute hydrochloric acid to afford a precipitate which was separated by filtration. Crystallization from methanol afforded the title compound (0.23 g, 0.67 mmol).

Workup

  1. temperaturewas heated
  2. customThe solvent was removed in vacuo and water
  3. additionwas added
  4. customto afford a precipitate which
  5. customwas separated by filtration
  6. customCrystallization from methanol

Sources & evidence

ORD record
ord-3dab6ea6f29d4ec6a19d26a7ef1c2820
Source dataset
uspto-grants-2013_05
Patent number
US08440705B2

Reaction notes

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