Potassium Carbonate → 2,2-Difluoro-1,3-dioxaindan-4-amine

HRID 1379253Notes

Reaction equation

HRID 1379253 reaction equation
Cl[C:2]1[C:12](Cl)=[CH:11][C:5]2[O:6][C:7]([F:10])([F:9])[O:8][C:4]=2[C:3]=1[N+:14]([O-])=O.C(=O)([O-])[O-].[K+].[K+].[H][H]>CO.[C].[Pd]>[NH2:14][C:3]1[C:4]2[O:8][C:7]([F:10])([F:9])[O:6][C:5]=2[CH:11]=[CH:12][CH:2]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 10967625HCID 10967625, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 27368912,2-Difluoro-1,3-dioxaindan-4-amine

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

68 g (250 mmol) of 5,6-dichloro-4-nitro-2,2-difluoro-benzo(1.3)dioxole, 69 g (500 mmol) of potassium carbonate and 5 g of palladium-carbon (10% strength) are stirred at 50° C. and a hydrogen pressure of 90 bar in 500 ml of methanol in an autoclave for 20 hours. The reaction mixture is filtered, the filtrate is mixed with 500 ml of water and extracted thoroughly with ether, the extract is dried over sodium sulphate and the ether is removed in a rotary evaporator. By distillation, 35 g (81% of theory) of 4-amino-2,2-difluoro-benzo(1.3)dioxole are obtained having a boiling point of 84° to 86° C./16 mm and a refractive index of nD21 : 1.4995.

Workup

  1. filtrationThe reaction mixture is filtered
  2. additionthe filtrate is mixed with 500 ml of water
  3. extractionextracted thoroughly with ether
  4. dry with materialthe extract is dried over sodium sulphate
  5. customthe ether is removed in a rotary evaporator
  6. distillationBy distillation, 35 g (81% of theory) of 4-amino-2,2-difluoro-benzo(1.3)dioxole
  7. customare obtained

Sources & evidence

ORD record
ord-4e28ec33023c480c9865afde9b460264
Source dataset
uspto-grants-1997_09
Patent number
US05670665

Reaction notes

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