Ammonium Chloride → HCID 89852603, compound

HRID 530216Notes

Reaction equation

HRID 530216 reaction equation
[NH4+].[Cl-].[N+:3]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]([C:16]#[N:17])=[C:9]2[NH:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:21][CH:20]=1)([O-])=O>CO.O.[Fe]>[NH2:3][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]([C:16]#[N:17])=[C:9]2[NH:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 89852229HCID 89852229, compound

Product 1

HCID 89852603HCID 89852603, compoundYield 75.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

Fe (2.9 g, 52.4 mmol, 4.0 eq) and NH4Cl was added to a solution of 6-nitro-4-((4-phenoxyphenyl)amino)quinoline-3-carbonitrile (5.0 g, 13.1 mmol, 1.0 eq) in methanol/water (50/50 mL). The mixture was heated to reflux for 8 hours, cool to room temperature and extracted with ethyl acetate (100×3 mL). The organic layers were combined, dried over anhydrous sodium sulfate. The crude product was purified by flash column chromatography on silica gel to give 6-amino-4-((4-phenoxyphenyl)amino)quinoline-3-carbonitrile (Compound 19) as a solid 3.5 g.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 8 hours
  3. extractionextracted with ethyl acetate (100×3 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe crude product was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-77c20674a63346cfa62674e8f4a94371
Source dataset
uspto-grants-2016_05
Patent number
US09353062B2

Reaction notes

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