Ammonium Chloride → HCID 58464827, compound

HRID 1185331Notes

Reaction equation

HRID 1185331 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH:8]=2)=[C:5]([N+:20]([O-])=O)[CH:4]=[N:3]1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:20][C:5]1[CH:4]=[N:3][N:2]([CH3:1])[C:6]=1[C:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:9][CH:8]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 58464760HCID 58464760, compound

Product 1

HCID 58464827HCID 58464827, compoundYield 64.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of tert-butyl 4-(1-methyl-4-nitro-1H-pyrazol-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (0.15 g, 0.48 mmol) in ethanol (10 mL) and water (1 mL) was added ammonium chloride (0.131 g, 2.44 mmol) and iron powder (0.109 g, 1.95 mmol). The mixture was heated at 100° C. for 1 hr. The mixture was cooled and filtered through celite and washed with EtOAc. The organic layer was washed with water, separated and dried over MgSO4. The solvent was removed under reduced pressure to yield tert-butyl 4-(4-amino-1-methyl-1H-pyrazol-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate as a brown oil (86 mg, 64%).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through celite
  3. washwashed with EtOAc
  4. washThe organic layer was washed with water
  5. customseparated
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-db3f3398f35a46b89281efd894934c65
Source dataset
uspto-grants-2014_03
Patent number
US08669361B2

Reaction notes

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