Ethanolamine → HCID 53259296, compound

HRID 876182Notes

Reaction equation

HRID 876182 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[CH2:17]([CH2:19][NH2:20])[OH:18]>CCOC(C)=O>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6]2[N:7]=[C:2]([NH:20][CH2:19][CH2:17][OH:18])[CH:3]=[CH:4][CH:5]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 53410281HCID 53410281, compound

Product 1

HCID 53259296HCID 53259296, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

190 mg of 6-chloro-N-(4-methoxyphenyl)pyridin-2-amine were mixed with 397 mg of ethanolamine and the mixture obtained was heated in a screw cap vial under argon at 150° C. for 3 days. The mixture obtained was cooled to r.t. and 5 mL of EtOAc were added, The mixture obtained was extracted with 5 mL of EtOAc for three times, the phases were separated, the organic phase was dried and from the dry mixture obtained solvent was evaporated off. The evaporation residue obtained was subjected to flash column chromatography (EtOAc:PE 3:1). 2-(6-(4-Methoxyphenylamino)pyridin-2-ylamino)ethan-1-ol was obtained in the form of a brown oil.

Workup

  1. customthe mixture obtained
  2. temperaturewas heated in a screw
  3. customcap vial under argon at 150° C. for 3 days
  4. customThe mixture obtained
  5. customThe mixture obtained
  6. extractionwas extracted with 5 mL of EtOAc for three times
  7. customthe phases were separated
  8. customthe organic phase was dried and from the dry mixture
  9. customobtained solvent
  10. customwas evaporated off
  11. customThe evaporation residue obtained

Sources & evidence

ORD record
ord-55f75ae921a44457a0ecf2a5c133891c
Source dataset
uspto-grants-2015_03
Patent number
US08986994B2

Reaction notes

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