4-Toluenesulfonyl chloride → HCID 178427409, compound

HRID 442340Notes

Reaction equation

HRID 442340 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH2:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[N:18][C:17]([C:23]([OH:25])=[O:24])=[C:16]2[OH:26]>CCOCC>[OH:26][C:16]1[C:15]2[C:20](=[CH:21][CH:22]=[C:13]([NH:12][S:7]([C:4]3[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=3)(=[O:9])=[O:8])[CH:14]=2)[N:19]=[N:18][C:17]=1[C:23]([OH:25])=[O:24]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 178507368HCID 178507368, compound

Product 1

HCID 178427409HCID 178427409, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of p-toluenesulphonyl chloride (7.0 g.) in ether (30 ml.) was added to a stirred solution of 6-amino-4-hydroxycinnolin-3-yl carboxylic acid (1.025 g.) in N-sodium hydroxide solution (15 ml.). The heterogeneous mixture was stirred vigorously for 16 hours. The aqueous phase was separated, washed with ether (2 × 25 ml.), and acidified to pH 2 with 5N-hydrochloric acid. The solid which separated was filtered off, washed with water and dried as much as possible on the filter. The product was purified by chromatography on a silica column (30 g., Kieselgel 60), eluted with a mixture of ethanol (15 parts by volume), chloroform (85 parts by volume) and formic acid (1 parts by volume), to give 4-hydroxy-6-(p-toluenesulphonylamino)cinnolin-3-yl carboxylic acid, m.p. 272°-273° C. EXAMPLE 16

Workup

  1. customThe aqueous phase was separated
  2. washwashed with ether (2 × 25 ml.)
  3. customThe solid which separated
  4. filtrationwas filtered off
  5. washwashed with water
  6. customdried as much as possible on the filter
  7. customThe product was purified by chromatography on a silica column (30 g., Kieselgel 60)
  8. washeluted with a mixture of ethanol (15 parts by volume), chloroform (85 parts by volume) and formic acid (1 parts by volume)

Sources & evidence

ORD record
ord-cc94ede2c1d44713948a5bffae169b8a
Source dataset
uspto-grants-1977_08
Patent number
US04045439

Reaction notes

Loading…