Ammonium Chloride → HCID 11791017, compound

HRID 1370321Notes

Reaction equation

HRID 1370321 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl[C:6]1[C:15]2[C:10](=[C:11]([O:18][CH3:19])[CH:12]=[CH:13][C:14]=2[O:16][CH3:17])[N:9]=[CH:8][CH:7]=1.[NH4+].[Cl-]>CN(C=O)C.O>[N:1]([C:6]1[C:15]2[C:10](=[C:11]([O:18][CH3:19])[CH:12]=[CH:13][C:14]=2[O:16][CH3:17])[N:9]=[CH:8][CH:7]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 2244024-Chloro-5,8-dimethoxyquinoline

Product 1

HCID 11791017HCID 11791017, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Conditions

Temperature
90 °C

Procedure

16.7 g of NaN3 are added to a solution of 10 g (44.7 mmol) of 4-chloro-5,8-dimethoxyquinoline in a DMF/H2O mixture (160 mL/60 mL). The reaction medium is heated at 90° C. for 2 h 30 min. After cooling, the mixture is hydrolyzed with 500 mL of saturated NH4Cl solution and is extracted with CHCl3 (3 times 150 mL) After drying over MgSO4, the organic phases are concentrated on a rotary evaporator and the DMF is then removed under vacuum (2 mmHg). 8.7 g of azide are obtained in the form of a brown powder.

Workup

  1. temperatureAfter cooling
  2. extractionis extracted with CHCl3 (3 times 150 mL)
  3. dry with materialAfter drying over MgSO4
  4. concentrationthe organic phases are concentrated on a rotary evaporator
  5. customthe DMF is then removed under vacuum (2 mmHg)

Sources & evidence

ORD record
ord-c70a93db83c44572a0962cdc5f0c7009
Source dataset
uspto-grants-2003_06
Patent number
US06583150B1

Reaction notes

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