Hydrochloric Acid → HCID 20131409, compound

HRID 1789061Notes

Reaction equation

HRID 1789061 reaction equation
[N+]([O-])(O)=O.[F:5][CH:6]([F:22])[O:7][C:8]1[C:13]([F:14])=[CH:12][C:11]([NH:15]C(=O)C)=[C:10]([N+:19]([O-])=O)[CH:9]=1.[ClH:23].FC(F)OC1C(F)=CC(N)=C([N+]([O-])=O)C=1>ClCCl.CO.C1CCCCC1>[ClH:23].[ClH:23].[F:22][CH:6]([F:5])[O:7][C:8]1[C:13]([F:14])=[CH:12][C:11]([NH2:15])=[C:10]([NH2:19])[CH:9]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 944Nitric AcidHCID 20131372HCID 20131372, compoundHCID 20131402HCID 20131402, compound

Product 1

HCID 20131409HCID 20131409, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolvent

Procedure

22.5 ml of 100% nitric acid are added dropwise at 20° C. within 30 min. to 20 g of the above compound in 200 ml of dichloromethane, and the mixture is stirred for a further 15 h at room temperature. Analogously to Example B7c, this gives N-(4-difluoromethoxy-5-fluoro-2-nitrophenyl)acetamide of m.p. 72°-74° C. (from cyclohexane) in 89% yield. By stirring for several hours with 1M hydrochloric acid in methanol at 60° C., 4-difluoromethoxy-5-fluoro-2-nitroaniline of m.p. 95°-97.5° C. is obtained in 95% yield and, analogously to Example B7e, 4-difluoromethoxy-5-fluoro-1,2-phenylenediamine dihydrochloride (decomposition from 210° C.) is obtained in 85% yield.

Sources & evidence

ORD record
ord-aa2d9d186baa4dec80079d17c6497e03
Source dataset
uspto-grants-1987_08
Patent number
US04686230

Reaction notes

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