Hydrochloric Acid → HCID 19385473, compound

HRID 2399360Notes

Reaction equation

HRID 2399360 reaction equation
[NH:1]([C:3]1[N:4]=[N:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([F:18])[F:17])=[C:11]([O:19][CH3:20])[CH:10]=2)=[CH:7][CH:8]=1)N.Cl.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:1][C:3]1[N:4]=[N:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([F:17])[F:18])=[C:11]([O:19][CH3:20])[CH:10]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2723923Ammonium formateHCID 19385493HCID 19385493, compound

Product 1

HCID 19385473HCID 19385473, compoundYield 63.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

5.0 g (18 mmol) of 3-hydrazino-6-(4-difluoromethoxy-3-methoxyphenyl)pyridazine are dissolved in 50 ml of ethanol and 2.3 ml (27 mmol) of concentrated hydrochloric acid, 1 g of palladium/carbon and 3.4 g (54 mmol) of ammonium formate are added, and the mixture is heated to 80° C. After evolution of gases has ceased, the mixture is stirred for a further 3 hours, filtered to remove the catalyst, and the solution is stirred in 1 l water and made alkaline with concentrated ammonia, and the resulting precipitate is collected on a suction funnel. The filter cake is thoroughly washed with water and then dried and chromatographed in a 95:5 mixture of dichloromethane/methanol on silica gel. The appropriate fractions are concentrated in vacuo. 3 g (63.6%) of 3-amino-6-(4-difluoromethoxy-3-methoxyphenyl)pyridazine of m.p. 184° C. are obtained.

Workup

  1. filtrationfiltered
  2. customto remove the catalyst
  3. stirringthe solution is stirred in 1 l water
  4. customthe resulting precipitate is collected on a suction funnel
  5. washThe filter cake is thoroughly washed with water
  6. customdried
  7. customchromatographed in a 95:5 mixture of dichloromethane/methanol on silica gel
  8. concentrationThe appropriate fractions are concentrated in vacuo

Sources & evidence

ORD record
ord-cebb52af42f04462a1475e0b654afef2
Source dataset
uspto-grants-1995_09
Patent number
US05449676

Reaction notes

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