Sodium Bicarbonate → HCID 58081223, compound

HRID 928433Notes

Reaction equation

HRID 928433 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH:12]=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[Li+].[BH4-].C([O-])(O)=O.[Na+]>C1COCC1>[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH2:12][OH:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 128710747-Methylquinoline-3-carbaldehyde

Product 1

HCID 58081223HCID 58081223, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 7-methyl-3-quinoline carboxaldehyde (200 mg, 1.168 mmol) in THF (4.5 ml) was added 2M LiBH4 solution in THF (2.337 ml, 4.67 mmol) at 0° C. Reaction mixture was stirred at 0° C. for 2 h, then slowly poured into NaHCO3 sat. solution and extracted twice with ethyl acetate. Organic layer was dried over sodium sulfate, filtered and evaporated to afford the crude material, which was purified by silica gel chromatography (cyclohexane/ethyl acetate form 100/0 to 0/100) to afford the title compound. HPLC (Method G) Rt=0.68 min, MS (Method V) [M+H]+=174.2.

Workup

  1. customReaction mixture
  2. extractionextracted twice with ethyl acetate
  3. dry with materialOrganic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto afford the crude material, which
  7. customwas purified by silica gel chromatography (cyclohexane/ethyl acetate form 100/0 to 0/100)

Sources & evidence

ORD record
ord-a43f647e869149aaa23a05e18bf87b9d
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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