Ammonium Chloride → HCID 19592360, compound

HRID 613492Notes

Reaction equation

HRID 613492 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][C:13]([C:17](OCC)=[O:18])=[C:12]2[O:22][CH2:23][CH3:24])=[O:5].[BH4-].[Li+].[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][C:13]([CH2:17][OH:18])=[C:12]2[O:22][CH2:23][CH3:24])=[O:5]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 19592876HCID 19592876, compound

Product 1

HCID 19592360HCID 19592360, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 8-(2,6-dichlorobenzoylamino)-4-ethoxy-3-ethoxycarbonylquinoline (179 mg) in tetrahydrofuran was added lithium borohydride (22.5 mg), and the mixture was stirred for 4 hours at 50° C. To the mixture was dropwise added saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer 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) to give 8-(2,6-dichlorobenzoylamino)-4-ethoxy-3-hydroxymethylquinoline (55.9 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate-n-hexane)

Sources & evidence

ORD record
ord-ef920c39ccc647cebe86fe8b0f7cabb3
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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