Sodium Hydroxide → 6-Hydroxy[1]benzofuro[3,2-c]pyridine-9-carbaldehyde-2-oxide

HRID 39333Notes

Reaction equation

HRID 39333 reaction equation
C1([O:6][C:7]2[C:12]3[O:13][C:14]4[CH:19]=[CH:18][N+:17]([O-:20])=[CH:16][C:15]=4[C:11]=3[C:10]([CH:21]=[O:22])=[CH:9][CH:8]=2)CCCC1.[OH-].[Na+]>Br.O>[OH:6][C:7]1[C:12]2[O:13][C:14]3[CH:19]=[CH:18][N+:17]([O-:20])=[CH:16][C:15]=3[C:11]=2[C:10]([CH:21]=[O:22])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 866431196-(Cyclopentyloxy)[1]benzofuro[3,2-c]pyridine-9-carbaldehyde 2-oxide

Product 1

HCID 251182786-Hydroxy[1]benzofuro[3,2-c]pyridine-9-carbaldehyde-2-oxideYield 80%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A well stirred suspension of 6-(cyclopentyloxy)[1]benzofuro[3,2-c]pyridine-9-carbaldehyde 2-oxide (200 mg, 0.671 mmol) in 48% aqueous hydrobromic acid (10 mL) was heated to 70-80° C. for 2-3 hours. The reaction mixture was cooled to room temperature and diluted with water (50 mL) and was made alkaline (pH=9-10) by means of a 10% aqueous solution of sodium hydroxide. It was then washed with ethyl acetate (2×25 mL). The aqueous layer was then acidified with acetic acid (pH=4-5) and stirred at 10-15° C. for 30-40 minutes. The solid obtained was filtered and dried to afford 6-hydroxy[1]benzofuro[3,2-c]pyridine-9-carbaldehyde-2-oxide (Yield=80-90%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washIt was then washed with ethyl acetate (2×25 mL)
  3. stirringstirred at 10-15° C. for 30-40 minutes
  4. customThe solid obtained
  5. filtrationwas filtered
  6. customdried

Sources & evidence

ORD record
ord-126cb5487f434bd3905237bb52f0569b
Source dataset
uspto-grants-2013_09
Patent number
US08524905B2

Reaction notes

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