Ammonium Chloride → HCID 178426833, compound

HRID 1292151Notes

Reaction equation

HRID 1292151 reaction equation
[C:1]([C:3]1[C:4](=[O:34])[NH:5][C:6]2[C:11]([CH:12]=1)=[C:10]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)[CH:16]=1)[CH:9]=[CH:8][C:7]=2[CH3:33])#[N:2].[N-:35]=[N+:36]=[N-:37].[Na+].[NH4+].[Cl-]>CN(C=O)C>[CH3:33][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)[CH:16]=2)=[C:11]2[C:6]=1[NH:5][C:4](=[O:34])[C:3]([C:1]1[NH:37][N:36]=[N:35][N:2]=1)=[CH:12]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 15411303HCID 15411303, compound

Product 1

HCID 178426833HCID 178426833, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A liquid mixture of 0.822 g (1.84 mmol) of the 3-cyano-8-methyl-5-[3-(2-quinolinylmethoxy)benzyloxy]-1,2-dihydroquinolin-2-one obtained in Example 3, 0.359 g (5.52 mmol) of NaN3, 0.295 g (5.52 mmol) of NH4Cl and 20 ml of DMF was stirred at a bath temperature of 120° C. for 8 hours. The solvent was distilled off and the residue was dissolved in a large amount of a CHCl3 --MeOH mixed solvent. The solution was washed with water and then dried over MgSO4. The solvent was distilled off, whereby 0.519 g of the title compound was obtained as pale yellow powder (yield: 57.5%).

Workup

  1. distillationThe solvent was distilled off
  2. dissolutionthe residue was dissolved in a large amount of a CHCl3
  3. washThe solution was washed with water
  4. dry with materialdried over MgSO4
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-f31447d2c105468794faa1a1873b3710
Source dataset
uspto-grants-1998_05
Patent number
US05756518

Reaction notes

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