1H-Indazol-6-amine → 4,5,6,7-tetrahydro-1H-indazol-6-amine

HRID 1013821Notes

Reaction equation

HRID 1013821 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH2:10])[CH:8]=2)[CH:3]=[N:2]1>C(O)C.[Rh]>[NH:1]1[C:9]2[CH2:8][CH:7]([NH2:10])[CH2:6][CH2:5][C:4]=2[CH:3]=[N:2]1

Participants

4

Reactant 1

HCID 814231H-Indazol-6-amine

Product 1

HCID 128984204,5,6,7-tetrahydro-1H-indazol-6-amineYield 37.4%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

Combine 1H-indazol-6-ylamine (12.45 g, 93.6 mmol) and 5% Rh/C (6.13 g) in ethanol (300 mL) and heat at 120° C. for 72 hours under ˜1000 psi H2. Cool the reaction and filter through hyflo. Remove the solvent in vacuo and purify the crude product with 10% 2 M NH3 in MeOH in CH2Cl2 and re-purify mixed fractions with 15% 2 M NH3 in MeOH in CH2Cl2 to afford 4.80 g (37%) of the titled product. MS (m/z): 138 (M+1).

Workup

  1. temperatureCool
  2. customthe reaction
  3. filtrationfilter through hyflo
  4. customRemove the solvent in vacuo
  5. custompurify the crude product with 10% 2 M NH3 in MeOH in CH2Cl2
  6. customre-purify
  7. additionmixed fractions with 15% 2 M NH3 in MeOH in CH2Cl2

Sources & evidence

ORD record
ord-b179e0045fb14e759aaef21a9b292f04
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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