Fuming sulfuric acid → Sulfuric Acid

HRID 1381280Notes

Reaction equation

HRID 1381280 reaction equation
ClC1C=C(C=CC=1)NCCC(O)=O.ClC1C=C2C(C(=O)CCN2)=CC=1.[OH:26][S:27]([OH:30])(=[O:29])=[O:28].O=S(=O)=O.F.[B:36]([F:39])([F:38])[F:37]>>[S:27](=[O:28])(=[O:26])([OH:30])[OH:29].[FH:37].[B:36]([F:39])([F:38])[F:37]

Participants

7

Reactant 4

HCID 24681Fuming sulfuric acidHCID 889747-Chloro-2,3-dihydro-4-quinoloneHCID 9855450Trifluoroborane HydrofluorideHCID 124709193-((3-Chlorophenyl)amino)propanoic acid

Product 3

HCID 1118Sulfuric AcidHCID 6356Boron trifluorideHCID 14917Hydrofluoric Acid

Procedure

It should, however, be noted that, in the particular case of the cyclisation of 3-(m-chloroanilino)propionic acid by polyphosphoric acid, a mixture of substantially equal quantities of 5-chloro- and 7-chloro-1,2,3,4-tetrahydro-4-quinolinone is obtained. The selectivity for 7-chloro-1,2,3,4-tetrahydro-4-quinolinone is significantly improved if an oleum or a hydrofluoric acid/boron trifluoride mixture is used as cyclisation agent, but the industrial use of these processes encounters difficulties which result either from the handling of large quantities of sulphuric acid or from the utilisation of a mixture of anhydrous hydrofluoric acid and boron trifluoride.

Workup

  1. customis obtained

Sources & evidence

ORD record
ord-ff019c51e3c24b779fec4d063a1af4d9
Source dataset
uspto-grants-1986_04
Patent number
US04585867

Reaction notes

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