Sodium Bicarbonate → HCID 68503853, compound

HRID 1712531Notes

Reaction equation

HRID 1712531 reaction equation
[CH3:1][C:2]1([CH3:17])[C:11]2[C:6](=[C:7]([C:12](OC)=[O:13])[CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:16])[CH2:3]1.[BH4-].[Li+].C(=O)(O)[O-].[Na+]>O1CCCC1.COC(C)(C)C>[OH:13][CH2:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[NH:5][C:4](=[O:16])[CH2:3][C:2]2([CH3:17])[CH3:1]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 68501471HCID 68501471, compound

Product 1

HCID 68503853HCID 68503853, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 3.72 g of methyl 4,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinoline-8-carboxylate in 100 ml of tetrahydrofuran is admixed with 1.83 g of lithium borohydride and then stirred at 50° C. over 1 hour. The reaction mixture is cooled to room temperature, diluted with tert-butyl methyl ether and stirred with saturated aqueous sodium bicarbonate solution until no more gas is formed. The phases are separated—the organic phase is washed with water, dried over sodium sulphate and concentrated by evaporation. The crude title compound is obtained as a brown-yellow oil from the residue. Rt=3.02.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customis formed
  3. washis washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-417a387ec2704c7183c34b390438e6e8
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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