Hydrochloric Acid → 6-Chloro-3-(hydroxymethyl)oxazolo(4,5-b)pyridin-2(3H)-one

HRID 258571Notes

Reaction equation

HRID 258571 reaction equation
[CH2:1]=[O:2].Cl.[Cl:4][C:5]1[CH:6]=[C:7]2[O:13][C:12](=[O:14])[NH:11][C:8]2=[N:9][CH:10]=1>O>[OH:2][CH2:1][N:11]1[C:8]2=[N:9][CH:10]=[C:5]([Cl:4])[CH:6]=[C:7]2[O:13][C:12]1=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 136144596-Chlorooxazolo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 214260726-Chloro-3-(hydroxymethyl)oxazolo(4,5-b)pyridin-2(3H)-oneYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8 parts of 38% formaldehyde solution and 25 parts of 2N hydrochloric acid are added to a solution of 8.5 parts of 6-chlorooxazolo-[4,5-b]-pyridin-2-(3H)-one in 60 parts of water, and the whole is stirred for 4 hours at 50° to 60° C. After cooling with ice, filtration is performed and the residue is washed with ice water. There are obtained 8.5 parts of 3-hydroxymethyl-6-chloro-oxazolo[ 4,5-b]pyridin-2-(3H)-one (85% of theory), m.p. 137°-139° C.

Workup

  1. temperatureAfter cooling with ice, filtration
  2. washthe residue is washed with ice water

Sources & evidence

ORD record
ord-0b89a3058bee48e3b6d1cac7a8a983e1
Source dataset
uspto-grants-1977_07
Patent number
US04033975

Reaction notes

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