Methanesulfonyl chloride → HCID 20150454, compound

HRID 568349Notes

Reaction equation

HRID 568349 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][C:7]1[CH:8]=[C:9]([C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=2)[CH:10]=[C:11]2[C:16]=1[NH:15][C:14](=[O:17])[CH:13]=[CH:12]2>N1C=CC=CC=1>[CH3:6][C:7]1[CH:8]=[C:9]([C:18]2[CH:23]=[CH:22][C:21]([NH:24][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:20][CH:19]=2)[CH:10]=[C:11]2[C:16]=1[NH:15][C:14](=[O:17])[CH:13]=[CH:12]2

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 20150455HCID 20150455, compound

Product 1

HCID 20150454HCID 20150454, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulphonyl chloride (0.15 cm3) was added dropwise to a stirred solution of 8-methyl-6-(4-aminophenyl)-2-(1H)-quinolone (0.47 g) (see Example 13) in pyridine (3 cm3) at room temperature. After 0.5 hours volatile material was removed in in vacuo and the residue was partitioned between water (50 cm3) and dichloromethane:methanol, 4:1 (50 cm3). The insoluble material was filtered off, washed with methanol (10 cm3) and dried to afford the title compound, m.p. 340°-343° (0.45 g).

Workup

  1. customAfter 0.5 hours volatile material was removed in in vacuo
  2. customthe residue was partitioned between water (50 cm3) and dichloromethane
  3. filtrationThe insoluble material was filtered off
  4. washwashed with methanol (10 cm3)
  5. customdried

Sources & evidence

ORD record
ord-8a98603878354e9e80320260a15feaba
Source dataset
uspto-grants-1988_03
Patent number
US04728654

Reaction notes

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