HCID 19592412, compound → HCID 19592718, compound

HRID 613532Notes

Reaction equation

HRID 613532 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][C:13](O)=[O:14])=[CH:9][CH:8]=[CH:7][C:6]=2[NH:16][C:17](=[O:26])[C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:25]>O1CCCC1>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][CH2:13][OH:14])=[CH:9][CH:8]=[CH:7][C:6]=2[NH:16][C:17](=[O:26])[C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:25]

Participants

3

Reactant 1

HCID 19592412HCID 19592412, compound

Product 1

HCID 19592718HCID 19592718, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-bromo-4-carboxymethyl-8-(2,6-dichlorobenzoylamino)quinoline (130 mg) in dry tetrahydrofuran was added 10M solution of borane-methyl sulfide complex in tetrahydrofuran (0.286 ml) at ambient temperature, and the mixture was stirred for 4 hours at the same temperature. The mixture was quenched by 1N hydrochloric acid and stirred for 1 hour at the same temperature. The mixture was extracted with ethyl acetate, and the extract was washed with saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate: n-hexane, 1:2, v/v) and crystallized from ethyl acetate-n-hexane to give 3-bromo-8-(2,6-dichlorobenzoylamino)-4-(2-hydroxyethyl)quinoline (68.4 mg).

Workup

  1. customThe mixture was quenched by 1N hydrochloric acid
  2. stirringstirred for 1 hour at the same temperature
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe extract was washed with saturated sodium bicarbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (ethyl acetate
  8. customn-hexane, 1:2, v/v) and crystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-04d071abf7ef456bb0bcd08d430d8123
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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