Water → (4-PHENYLPYRIDIN-2-YL)METHANOL

HRID 2309356Notes

Reaction equation

HRID 2309356 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([C:13](N)=[O:14])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(=O)(O)(O)O.O>C1(C)C=CC=CC=1>[C:1]1([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][OH:14])[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1004Phosphoric AcidHCID 20184984HCID 20184984, compound

Product 1

HCID 12217651(4-PHENYLPYRIDIN-2-YL)METHANOLYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The procedure of Example 1 was used except that the catholyte was prepared from the following weight parts: 4-phenylpicolinamide (0.3), phosphoric acid (0.9), water (2.0), and toluene (0.8). The reduction was carried out similarly to Example 1 to give a 71% yield of 4-phenyl-2-pyridylcarbinol at 5.8 F/mole charge passage. Repeating the reduction with no toluene added gave a 49% yield of carbinol at 6 F/mole charge passage. Addition of a titanium salt to the catholyte containing added toluene resulted in a 55% yield of 4-phenyl-2-picolylamine by HPLC analysis. Other cathode materials than lead were also used successfully such as cadmium or zinc with similar results.

Workup

  1. customwas prepared from the following weight parts

Sources & evidence

ORD record
ord-6ae6fcb0d2634aeb96a5cd9aec181e62
Source dataset
uspto-grants-1987_09
Patent number
US04695352

Reaction notes

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