Sodium Azide → HCID 5328871, compound

HRID 1935153Notes

Reaction equation

HRID 1935153 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:23]#[N:24])[CH:5]=[CH:6][CH:7]=1.N([O-])=O.[Na+].[N-:29]=[N+:30]=[N-].[Na+]>C(O)(=O)C.O.C(OCC)(=O)C>[N:1]([C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:23]#[N:24])[CH:5]=[CH:6][CH:7]=1)=[N+:29]=[N-:30]

Participants

7

Reactant 3

HCID 33557Sodium AzideHCID 5328848HCID 5328848, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 5328871HCID 5328871, compoundYield 75.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Dissolved 643 mg (2.00 mmol) 4-(3-amino-phenylamino)-6,7-dimethoxy-quinoline-3-carbonitrile in 25 ml 80% acetic acid in water. Chilled to 0° C. and added 152 mg (2.21 mmol) sodium nitrite in 2.2 ml water. After 10 minutes, added 144 mg (2.21 mmol) sodium azide in 2.2 ml water. At 1.5 hours stripped solvent and dissolved residue in hot ethyl acetate. Washed with saturated sodium bicarbonate, water and brine and dried with sodium sulfate. Stripped solvent and redissolved in 60% ethyl acetate/methylene chloride and filtered through a pad of silica gel. Stripped solvent and dried in vacuo, giving 526 mg of brown solid: mass spectrum (electrospray m/e): M+H=347.1.

Workup

  1. waitAt 1.5 hours stripped
  2. washWashed with saturated sodium bicarbonate, water and brine
  3. dry with materialdried with sodium sulfate
  4. dissolutionredissolved in 60% ethyl acetate/methylene chloride
  5. filtrationfiltered through a pad of silica gel
  6. customdried in vacuo

Sources & evidence

ORD record
ord-aa489076e16a4bdda5b4b26600da8639
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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