Sulfuric Acid → 3,6-Dichlorocarbazole

HRID 1725318Notes

Reaction equation

[ClH:1].[ClH:2].[C:3]1([C:10]2[CH:16]=[CH:15][C:13](N)=[CH:12][CH:11]=2)[CH:9]=[CH:8][C:6](N)=[CH:5][CH:4]=1.[N+:17]([O-])([O-])=O.[K+].S(=O)(=O)(O)O>>[Cl:1][C:8]1[CH:6]=[CH:5][C:4]2[NH:17][C:16]3[C:10]([C:3]=2[CH:9]=1)=[CH:11][C:12]([Cl:2])=[CH:13][CH:15]=3

Participants

Reactant 3

HCID 1118Sulfuric Acid

HCID 10754Benzidine dihydrochloride

HCID 24434Potassium Nitrate

Product 1

HCID 2364873,6-Dichlorocarbazole

Procedure

Reaction of benzidine dihydrochloride (CAS 531-85-1) with potassium nitrate and sulfuric acid gives compound 1 (Zhurn. Obsh Khim., 1944, 14, 1019). Reaction of compound 1 with iron and hydrochloric acid leads to compound 2 (Zhurn. Obsh Khim., 1944, 14, 1019). Reaction of compound 2 with sulfuric acid affords 9H-carbazole-2,7-diamine 1-1 (Zhum. Obsh Khim., 1944, 14, 1019).

Sources & evidence

ORD record: ord-783c5d7696674021ac25679bf44a1572
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491245B2

Reaction notes

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