Ammonium Chloride → HCID 86708639, compound

HRID 921757Notes

Reaction equation

HRID 921757 reaction equation
[OH:1][C@H:2]([CH3:18])[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:13]([O-])=O)=[CH:10][CH:11]=2)[C:6]([C:16]#[N:17])=[N:5]1.[Cl-].[NH4+]>CCO.O.[Fe]>[NH2:13][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[N:4]([CH2:3][C@H:2]([OH:1])[CH3:18])[N:5]=[C:6]2[C:16]#[N:17]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86708638HCID 86708638, compound

Product 1

HCID 86708639HCID 86708639, compoundYield 74.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A solution of (R)-1-(2-hydroxypropyl)-5-nitro-1H-indazole-3-carbonitrile (0.76 g, 2.93 mmol) in EtOH (10 ml) was added to a suspension of iron (powder) (1.310 g, 23.46 mmol) and ammonium chloride (1.569 g, 29.3 mmol) in water (10 ml). The reaction mixture was heated in a microwave reactor at 80° C. for 15 min. The reaction vial was cooled to room temperature and the reaction mixture was filtered through celite, rinsing with EtOH, water, EtOH again, and then EtOAc. The filtrates were combined and diluted with EtOAc. The organic layer was washed with saturated aq. NaHCO3 solution, water, then brine, then dried over MgSO4, filtered, and evaporated to dryness. (R)-5-amino-1-(2-hydroxypropyl)-1H-indazole-3-carbonitrile (470 mg) was obtained as a pale yellow solid.

Workup

  1. customThe reaction
  2. temperaturevial was cooled to room temperature
  3. filtrationthe reaction mixture was filtered through celite
  4. washrinsing with EtOH, water, EtOH again
  5. additiondiluted with EtOAc
  6. washThe organic layer was washed with saturated aq. NaHCO3 solution, water
  7. dry with materialbrine, then dried over MgSO4
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-1ad7b2b6c5cd46a7a172d3db2657bd98
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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