HCID 19864523, compound → HCID 19864518, compound

HRID 1199995Notes

Reaction equation

HRID 1199995 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[N+:17]([O-])=O)=[CH:6][CH:5]=1>C(O)C>[NH2:17][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:11]=1[NH:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][OH:1])=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 19864523HCID 19864523, compound

Product 1

HCID 19864518HCID 19864518, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-[4-(2-Hydroxyethyl)phenylamino]-3-nitropyridine (5.18 g) and stannous chloride dihydrate (22.56 g) were suspended in ethanol (100 ml) and heated at reflux for 45 minutes. The mixture was concentrated under vacuum, basified to pH8 with 2M sodium hydroxide solution and then extracted with ethyl acetate (3×200 ml). The combined organic extracts were dried over Na2SO4, filtered and evaporated under vacuum to give the crude product, (4.5 g), which was used directly in the next step.

Workup

  1. temperatureheated
  2. temperatureat reflux for 45 minutes
  3. concentrationThe mixture was concentrated under vacuum
  4. extractionextracted with ethyl acetate (3×200 ml)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-d024b8760f7c4395b8fbb92b7ae9a945
Source dataset
uspto-grants-1990_02
Patent number
US04904671

Reaction notes

Loading…