2-Pyridinecarboxaldehyde → HCID 22618245, compound

HRID 842110Notes

Reaction equation

HRID 842110 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]3[C:16]([NH2:17])=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)[CH:5]=[CH:6][CH:7]=1.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH:24]=O.C([BH3-])#N.[Na+].[OH-].[Na+]>CO.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]3[C:16]([NH:17][CH2:24][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=4)=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 142732-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 22618269HCID 22618269, compound

Product 1

HCID 22618245HCID 22618245, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 887MethanolSolvent3×

Procedure

To a stirred suspension of 2-(3-chlorophenyl)-7-amino-benzoxazole (1.10 g, 0.0045 mol) in 10 ml of methanol, 2.5 ml of 1 N HCl in methanol, was added. 2-pyridinecarboxaldehyde(0.043 g, 0.0040 mol) was added to this suspension followed by sodium cyanoborohydride (0.32 g, 0.0051 mol) and the pH was adjusted to 6 using 1 N HCl in methanol. After 1 hour, 1 N sodium hydroxide was added to bring the pH to 10 and the reaction was extracted with 3×50 ml of ethyl acetate. The combined ethyl acetate extractions were washed with water, dried and evaporated to give 1.3 g of yellow solid. This solid was purified by flash chromatography over silica gel using 50:50 CH2Cl2 in hexane to give 0.25 g of recovered starting material, followed by 0.90 g of product when the eluting solvent was CH2Cl2. This solid was recrystallized from 100 ml of hexane to give 0.78 g of the title compound, mp 115-116° C.

Workup

  1. additionwas added
  2. extractionthe reaction was extracted with 3×50 ml of ethyl acetate
  3. extractionThe combined ethyl acetate extractions
  4. washwere washed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-d625b6488e354b44833e5f45371b3dd6
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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