Sodium borohydride → HCID 14368433, compound

HRID 1762189Notes

Reaction equation

HRID 1762189 reaction equation
[CH:1]([C:3]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]=[O:21])[C:4]=1[CH2:5][O:6][C:7]1[C:8]([N+:13]([O-:15])=[O:14])=[N:9][CH:10]=[CH:11][CH:12]=1)=[O:2].C(C1C=CC=C(C)C=1COC1C([N+]([O-])=O)=NC=CC=1)=O.[BH4-].[Na+]>C(O)C>[OH:2][CH2:1][C:3]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:4]=1[CH2:5][O:6][C:7]1[C:8]([N+:13]([O-:15])=[O:14])=[N:9][CH:10]=[CH:11][CH:12]=1.[OH:21][CH2:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:3]([CH2:1][OH:2])[C:4]=1[CH2:5][O:6][C:7]1[C:8]([N+:13]([O-:15])=[O:14])=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 20042527HCID 20042527, compoundHCID 20042539HCID 20042539, compound

Product 2

HCID 14368433HCID 14368433, compoundHCID 14368434HCID 14368434, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of a mixture (1.29 g) of 3-(2,6-diformylbenzyloxy)-2-nitropyridine and 3-(2-formyl-6-methylbenzyloxy)-2-nitropyridine in ethyl alcohol (30 ml) was added portionwise sodium borohydride (390 mg) with ice-cooling. After being stirred for 3 hours with ice-cooling, the reaction mixture was poured into ice-water and the resulting precipitates were filtrated off. The precipitates were subjected to column chromatography on silica gel (40 g), eluting with a mixture of chloroform and methanol (20:1) to give 3-(2-hydroxymethyl-6-methylbenzyloxy)-2-nitropyridine (330 mg) and 3-[2,6-bis(hydroxymethyl)benzyloxy]-2-nitropyridine (700 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. customthe resulting precipitates
  4. filtrationwere filtrated off
  5. washeluting with a mixture of chloroform and methanol (20:1)

Sources & evidence

ORD record
ord-b4166de9190b435ea5417425e4ef7a40
Source dataset
uspto-grants-1989_05
Patent number
US04831041

Reaction notes

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