Hydrochloric Acid → HCID 21846057, compound

HRID 619119Notes

Reaction equation

HRID 619119 reaction equation
C(N(CC)CC)C.[C:8]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:20])[C:15](=[O:21])[CH:14]=[C:13]2[CH2:22][C:23](O)=[O:24])#[N:9].ClC(OCC)=O.[BH4-].[Na+].Cl>CO.O1CCCC1>[C:8]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:20])[C:15](=[O:21])[CH:14]=[C:13]2[CH2:22][CH2:23][OH:24])#[N:9]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 21846034HCID 21846034, compound

Product 1

HCID 21846057HCID 21846057, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

0.22 ml (1.58 mmol) of triethylamine is added to a suspension of 0.365 g (1.51 mmol) of 6-cyano-1-methyl-2-oxo-1,2-dihydro-4-quinolineacetic acid in 10 ce of tetrahydrofuran at -10° C., and 0.16 ml (1.6 mmol) of ethyl choroformate is then added dropwise. After stirring at -10° C. for 45 minutes, the reaction medium is filtered and the solids are rinsed with 3×8 ml of tetrahydrofuran. 0.25 g (6.61 mmol) of sodium borohydride and then 0.94 ml of methanol are added to the filtrate at 5-10° C. After stirring at 5-10° C. for 2 hours, 13 ml of 1 N aqueous hydrochloric acid solution are added. The mixture is extracted with is dichloromethane and then with ethyl acetate. The organic phases are dried over sodium sulphate and then concentrated under vacuum.

Workup

  1. filtrationthe reaction medium is filtered
  2. washthe solids are rinsed with 3×8 ml of tetrahydrofuran
  3. stirringAfter stirring at 5-10° C. for 2 hours
  4. extractionThe mixture is extracted
  5. dry with materialThe organic phases are dried over sodium sulphate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-37278481e19d43a18a9386f07e046676
Source dataset
uspto-grants-1999_09
Patent number
US05958924

Reaction notes

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