Ammonium Chloride → HCID 86708639, compound

HRID 1430938Notes

Reaction equation

HRID 1430938 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 rt 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 rt
  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-5f56580dc0ee4f7b9273872d98585dce
Source dataset
uspto-grants-2015_01
Patent number
US08940736B2

Reaction notes

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