3-Chloropropionic acid → HCID 66631508, compound

HRID 931830Notes

Reaction equation

HRID 931830 reaction equation
[Cl:1][CH2:2][CH2:3]C(O)=O.[Br:7][C:8]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2.[BH4-].[Na+]>C1COCC1.C(OCC)(=O)C>[Br:7][C:8]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]2[C:9]=1[CH2:10][CH2:11][CH2:12][N:13]2[CH2:3][CH2:2][Cl:1]

Participants

6

Reactant 3

HCID 78993-Chloropropionic acidHCID 709748-Quinolinol, 5-bromo-HCID 4311764Sodium borohydride

Product 1

HCID 66631508HCID 66631508, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

In a round bottom flask, 3-chloropropanoic acid (8.44 g, 89.3 mmol, 20 eq.) was added to 5-bromoquinolin-8-ol (1 g, 4.46 mmol, 1 eq.) in 15 mL THF at 0° C. NaBH4 (759 mg, 20 mmol, 4.5 eq.) was added portionwise in 50 minutes at 0° C. The reaction was stirred at 0° C. for 30 minutes then heated to 80° C. for 2 hours. The reaction was cooled down. Reaction mixture was diluted with ethyl acetate and washed with brine, dried (MgSO4), filtered, concentrated to give 5-bromo-1-(2-chloroethyl)-1,2,3,4-tetrahydroquinolin-8-ol crude. LCMS-ESI+ (m/z): [M+H]+ calcd for C11H14BrClNO: 291.58. found: 292.0.

Workup

  1. temperaturethen heated to 80° C. for 2 hours
  2. temperatureThe reaction was cooled down
  3. customReaction mixture
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8c453f2704624b41ba922113d99d4005
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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