Ethanol → HCID 67259831, compound

HRID 79259Notes

Reaction equation

HRID 79259 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([N+:17]([O-])=O)[CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:20][CH3:21])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].C(O)C>[Fe].O>[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:17])[C:11]=2[C:10]([CH2:20][CH3:21])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 67259581HCID 67259581, compound

Product 1

HCID 67259831HCID 67259831, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 1-benzyl-3-ethyl-4-nitro-1H-indazole (46.0 mg, 0.164 mmol), iron powder (91.3 mg, 1.64 mmol) and ammonium chloride (4.4 mg, 0.082 mmol) was stirred in a 4:1 mixture of ethanol and water (5 mL) with heating to 85° C. for 60 minutes. The solvent was removed under reduced pressure. Ethyl acetate (4 mL) and triethylamine (1 mL) was added and the mixture was heated for 15 minutes at 85° C. After cooling, the mixture was filtered through glass fiber filter paper, rinsing with methanol, dichloromethane and ethyl acetate. The filtrate was concentrated under reduced pressure to provide 1-benzyl-3-ethyl-1H-indazol-4-amine as an oil (40 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionEthyl acetate (4 mL) and triethylamine (1 mL) was added
  3. temperaturethe mixture was heated for 15 minutes at 85° C
  4. temperatureAfter cooling
  5. filtrationthe mixture was filtered through glass fiber
  6. filtrationfilter paper
  7. washrinsing with methanol, dichloromethane and ethyl acetate
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e6fae5492da24fd1b1c3bbc42bdb3962
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

Loading…