Ammonium Chloride → HCID 67261688, compound

HRID 79429

Reaction equation

HRID 79429 reaction equation
[CH:1]1([C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=3[N+:13]([O-])=O)[N:6]([CH2:16][C:17]3[C:18](=[O:24])[N:19]([CH3:23])[CH:20]=[CH:21][CH:22]=3)[N:5]=2)[CH2:3][CH2:2]1.[Cl-].[NH4+]>C(O)C.O.C(OCC)(=O)C.[Fe]>[NH2:13][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[C:4]([CH:1]1[CH2:3][CH2:2]1)=[N:5][N:6]2[CH2:16][C:17]1[C:18](=[O:24])[N:19]([CH3:23])[CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 672604333-((3-Cyclopropyl-4-nitro-1H-indazol-1-yl)methyl)-1-methylpyridin-2(1H)-one

Product 1

HCID 67261688HCID 67261688, compound

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

3-((3-Cyclopropyl-4-nitro-1H-indazol-1-yl)methyl)-1-methylpyridin-2(1H)-one (413 mg, 1.27 mmol) was dissolved in a mixture of ethanol (6.8 mL) and water (1.7 mL). Ammonium chloride (34 mg; 0.63 mmol) and iron powder (709 mg; 12.7 mmol) were added and the mixture was stirred with heating to 75° C. under a nitrogen atmosphere for 16 hours. The mixture was allowed to cool, diluted with ethyl acetate (50 mL) and filtered through a pad of Celite®. The filtrate was concentrated under reduced pressure to give the crude product as a colored oil. Purification using a silica gel preparative thin layer chromatography plate (20×20 cm, 2 mm) developed in a chamber with 40% ethyl acetate/dichloromethane, drying, and eluting with 80% ethyl acetate/dichloromethane gave 3-((4-amino-3-cyclopropyl-1H-indazol-1-yl)methyl)-1-methylpyridin-2(1H)-one as a viscous oil which began to crystallize upon drying under high vacuum (175 mg).

Workup

  1. temperatureto cool
  2. filtrationfiltered through a pad of Celite®
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto give the crude product as a colored oil
  5. customPurification
  6. customdrying
  7. washeluting with 80% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-4903f67422a540e19ea4e8771cceb365
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Linked notes

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