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

HRID 1013818

Reaction equation

HRID 1013818 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[NH2:10])[CH:3]=[N:2]1>C(O)C.[Rh]>[NH:1]1[C:9]2[CH:8]([NH2:10])[CH2:7][CH2:6][CH2:5][C:4]=2[CH:3]=[N:2]1

Participants

4

Reactant 1

HCID 889011H-indazol-7-amine

Product 1

HCID 219419624,5,6,7-tetrahydro-1H-indazol-7-amineYield 28%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

Combine 1H-indazol-7-ylamine (5.0 g, 37.6 mmol) and 5% Rh/C (2.45 g) in ethanol (120 mL) and heat at 120° C. for 48 hours under ˜1000 psi H2. Cool the reaction and filter through hyflo. Remove the solvent in vacuo and purify the crude product with 5% 2 M NH3 in MeOH in CH2Cl2 to afford 1.43 g (28%) 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 5% 2 M NH3 in MeOH in CH2Cl2

Sources & evidence

ORD record
ord-0c2ef847358947b4850acc0bc880c4ca
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Linked notes

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