Hydrochloric Acid → HCID 20131409, compound

HRID 1584004Notes

Reaction equation

HRID 1584004 reaction equation
[ClH:1].[F:2][CH:3]([F:16])[O:4][C:5]1[C:11]([F:12])=[CH:10][C:8]([NH2:9])=[C:7]([N+:13]([O-])=O)[CH:6]=1>CO>[ClH:1].[ClH:1].[F:16][CH:3]([F:2])[O:4][C:5]1[C:11]([F:12])=[CH:10][C:8]([NH2:9])=[C:7]([NH2:13])[CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20131402HCID 20131402, compound

Product 1

HCID 20131409HCID 20131409, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

22.5 ml of 100% strength nitric acid are added dropwise to 20 g of the above compound in 200 ml of methylene chloride at 20° C. in the course of 30 min., and stirring is continued for 15 h at room temperature. Analogously to Examples 11c, N-(4-difluoroethoxy-5-fluoro-2-nitrophenyl)-acetamide of m.p. 72°-74° C. (89% yield, from cyclohexane), is obtained. Stirring this compound for several hours with 1M hydrogen chloride in methanol at 60° C. yields 4-difluoromethoxy-5-fluoro-2-nitroaniline of m.p. 95°-97,5° C. (95% yield), and further reaction analogously to Example 11e gives 4-difluoromethoxy-5-fluoro-1,2-phenylenediamine dihydrochloride (85% yield, decomposition at 210° C.)

Workup

  1. customyields

Sources & evidence

ORD record
ord-8ba3dd9de1c6434799a098067eba5d99
Source dataset
uspto-grants-1985_11
Patent number
US04555518

Reaction notes

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