Acetic Acid → Quinoline, 1,2-dihydro-1-acetyl-

HRID 2375262Notes

Reaction equation

HRID 2375262 reaction equation
[BH4-].[Na+].[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[C:13](O)(=[O:15])[CH3:14]>C(OC(=O)C)(=O)C>[C:13]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH2:4]1)(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7047QuinolineHCID 4311764Sodium borohydride

Product 1

HCID 82423Quinoline, 1,2-dihydro-1-acetyl-

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
0 °C

Procedure

23.43 g of sodium borohydride are introduced, in portions, into a solution of 20 g of quinoline in 200 ml of acetic acid and 77.5 ml of acetic anhydride, cooled to 0° C. The mixture is then heated for 2 hours at 60° C. and is stirred overnight at ambient temperature. The mixture is concentrated, diluted with water, adjusted to pH=10 with sodium hydroxide solution and extracted with ether. The combined ethereal phases are washed with 1N hydrochloric acid and then at neutral pH and after conventional treatment the expected product is isolated.

Workup

  1. temperatureThe mixture is then heated for 2 hours at 60° C.
  2. concentrationThe mixture is concentrated
  3. additiondiluted with water
  4. extractionextracted with ether
  5. washThe combined ethereal phases are washed with 1N hydrochloric acid

Sources & evidence

ORD record
ord-4707817f93c148b0b928bdfda3a0aca8
Source dataset
uspto-grants-2008_12
Patent number
US07465733B2

Reaction notes

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