Acetic Acid → HCID 29228896, compound

HRID 389274Notes

Reaction equation

HRID 389274 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:14]([NH2:16])[CH3:15].C(O)(=O)C.C([BH3-])#N.[Na+].C([O-])(O)=O.[Na+]>CO>[Cl:1][C:2]1[C:11]([CH2:12][NH:16][CH2:14][CH3:15])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 6341EthylamineHCID 516892Sodium BicarbonateHCID 6909582-Chloro-3-quinolinecarboxaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 29228896HCID 29228896, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Chloro-3-quinolinecarboxaldehyde (2.0 g, 10.4 mmol), ethylamine (2M in MeOH, 5.2 mL, 10.4 mmol), and acetic acid (0.65 mL, 11.4 mmol) were combined in MeOH (15 mL) and stirred at room temperature for 30 minutes until all materials were completely dissolved. Sodium cyanoborohydride (1.31 g, 20.9 mmol) was added portionwise over 5 minutes, and the reaction was stirred for 1 hour. The mixture was worked-up with saturated aqueous NaHCO3 and extracted with CH2Cl2, and the residue was purified by silica gel chromatography (0-5% MeOH in CH2Cl2) to give the title compound.

Workup

  1. dissolutionwere completely dissolved
  2. stirringthe reaction was stirred for 1 hour
  3. extractionextracted with CH2Cl2
  4. customthe residue was purified by silica gel chromatography (0-5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-39a3cd8e63cd48bdadfe5b2d0487346f
Source dataset
uspto-grants-2013_02
Patent number
US08378107B2

Reaction notes

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