Hydrochloric Acid → HCID 21536791, compound

HRID 1076452Notes

Reaction equation

HRID 1076452 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7](N)=[C:6]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=1)([O-:3])=[O:2].N([O-])=O.[Na+].[ClH:22]>CN(C)C=O>[C:12]1([O:11][C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=[CH:9][C:7]=2[Cl:22])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 2233294-nitro-2-phenoxyanilineHCID 23668193Sodium Nitrite

Product 1

HCID 21536791HCID 21536791, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Nitro-2-phenoxyaniline was dissolved in N,N-dimethylformamide and hydrochloric acid and diazotized with sodium nitrite. The resulting slurry was added to a solution of cuprous chloride in hydrochloric acid to give a 60-70% yield of 2-chloro-5-nitrophenyl phenyl ether, b2-3 180°-90°, m. 73°-5°. This was converted to N-(4-nitro-2-phenoxyphenyl)-pyrrolidine, m. ca. 90°, by refluxing with excess pyrrolidine in 94-97% yield. Catalytic reduction followed by treatment with hydrochloric acid then gave N-(4-amino-2-phenoxyphenyl)pyrrolidine hydrochloride, which was slurried with water and diazotized conventionally with sodium nitrite. The clarified diazonium chloride solution was finally treated with hexafluoroarsenic acid to precipitate the desired 3-phenoxy-4-(1-pyrrolidinyl)benzenediazonium hexafluoroarsenate, m. 138°-140° (dec.), E395 36,3000) in 96% of the yield calculated from the amount of N-(4-nitro-2-phenoxyphenyl)pyrrolidine charged to the catalytic reduction preceding the diazotization.

Sources & evidence

ORD record
ord-d672dc7635db40a5bae3b193032eccbd
Source dataset
uspto-grants-1976_05
Patent number
US03957489

Reaction notes

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