Glycolic Acid → (3H-imidazo(4,5-b)pyridin-2-yl)methanol

HRID 2083986Notes

Reaction equation

HRID 2083986 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9](O)(=O)[CH2:10][OH:11].O>C1(C)C=C(C)C=C(C)C=1>[OH:11][CH2:10][C:9]1[NH:8][C:7]2[CH:6]=[CH:5][CH:4]=[N:3][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 757Glycolic AcidHCID 962WaterHCID 99562,3-Diaminopyridine

Product 1

HCID 1282496(3H-imidazo(4,5-b)pyridin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 7947MesityleneSolvent

Procedure

using a Dan-Stark separator, 2,3-diaminopyridine (54.6 g; 0.5 mol) and glycolic acid (38 g; 0.5 mol) in 700 ml of mesitylene were boiled under reflux until the calculated amount of water had separated off. The mixture was then cooled to room temperature, and the resulting precipitate was filtered off with suction and, with addition of activated carbon, boiled in 800 ml of water for 15 min. The hot suspension was filtered and once more cooled to room temperature, and the colourless crystals that precipitated out were filtered off with suction and dried. Yield: 56.4 g (75%).

Workup

  1. customhad separated off
  2. filtrationthe resulting precipitate was filtered off with suction and, with addition of activated carbon
  3. filtrationThe hot suspension was filtered
  4. temperatureonce more cooled to room temperature
  5. customthe colourless crystals that precipitated out
  6. filtrationwere filtered off with suction
  7. customdried

Sources & evidence

ORD record
ord-ccbd2eccc5e24b8bb077e0f6077b6835
Source dataset
uspto-grants-2004_04
Patent number
US06716849B1

Reaction notes

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