Ammonium Chloride → HCID 66958168, compound

HRID 1887718Notes

Reaction equation

HRID 1887718 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[C:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH:14]=1)([O-])=O.[Cl-].[NH4+]>[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[C:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH:14]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 66958157HCID 66958157, compound

Product 1

HCID 66958168HCID 66958168, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Conditions

Temperature
70 °C

Procedure

To a solution of 25 mL dioxane, 19 mL ethanol and 12 mL distilled water was added tert-butyl 4-(5-nitro-1H-indazol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (618 mg, 1.79 mmol). To the mixture was added powdered iron (0) (502 mg, 5.0 eq) and ammonium chloride (385 mg, 4.0 eq). The reaction was heated to 70° C. under argon for 3 h. The reaction was cooled, filtered and washed with MeOH. The solvent was removed to obtain the crude which was purified by silica gel chromatography to afford the desired compound tert-butyl 4-(5-amino-1H-indazol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate.

Workup

  1. distillationTo a solution of 25 mL dioxane, 19 mL ethanol and 12 mL distilled water
  2. additionTo the mixture was added
  3. temperatureThe reaction was cooled
  4. filtrationfiltered
  5. washwashed with MeOH
  6. customThe solvent was removed
  7. customto obtain the crude which
  8. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-63fa06725c4840318af607a2ede5befa
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

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