Sodium Hydroxide → HCID 19896786, compound

HRID 1031455Notes

Reaction equation

HRID 1031455 reaction equation
[CH3:1][C:2]1([CH3:23])[C:11]2[CH:10]=[C:9]3[NH:12][C:13]([C:15]4[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=4)=[N:14][C:8]3=[CH:7][C:6]=2[NH:5][C:4](=[O:22])[CH2:3]1.[CH3:24][S:25](Cl)(=[O:27])=[O:26].[OH-].[Na+]>O>[CH3:1][C:2]1([CH3:23])[C:11]2[CH:10]=[C:9]3[NH:12][C:13]([C:15]4[CH:20]=[CH:19][C:18]([O:21][S:25]([CH3:24])(=[O:27])=[O:26])=[CH:17][CH:16]=4)=[N:14][C:8]3=[CH:7][C:6]=2[NH:5][C:4](=[O:22])[CH2:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 135776339HCID 135776339, compound

Product 1

HCID 19896786HCID 19896786, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2 g. (6.5 mmole) 8,8-dimethyl-2-(4-hydroxyphenyl)-5,6,7,8-tetrahydro-lH-imidazo[4,5-g]quinolin-6-one (see Example 30 d)) were suspended in 10 ml. water and, while cooling with ice, 5 ml. (65 mmole) methanesulphonic acid chloride and 50 ml. 2N aqueous sodium hydroxide solution were alternatingly added dropwise thereto in such a manner that a pH value of about 10 to 13 was always present. When the reaction was completed, the reaction mixture was filtered off with suction, the product was washed with water and purified by column chromatography (elution agent: methylene chloride/ methanol/acetic acid; 10:1:0.2 v/v/v). The evaporation fractions were suspended in water, rendered ammoniacal and washed with water to give 1.5 g. (68% of theory) of the title compound; m.p. 209 -215° C.

Workup

  1. filtrationthe reaction mixture was filtered off with suction
  2. washthe product was washed with water
  3. custompurified by column chromatography (elution agent: methylene chloride/ methanol/acetic acid; 10:1:0.2 v/v/v)
  4. customThe evaporation fractions
  5. washwashed with water
  6. customto give 1.5 g

Sources & evidence

ORD record
ord-da133ddc253940c0b4c4d47234709286
Source dataset
uspto-grants-1990_09
Patent number
US04954498

Reaction notes

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