Sodium Hydroxide → HCID 18958954, compound

HRID 1708557Notes

Reaction equation

HRID 1708557 reaction equation
[CH3:1][C:2]1[N:3]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20]CC)=[O:19])=[CH:13][CH:12]=2)[C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=1.[OH-].[Na+]>C(O)C.O>[CH3:1][C:2]1[N:3]([C:11]2[CH:12]=[CH:13][C:14]([CH2:17][C:18]([OH:20])=[O:19])=[CH:15][CH:16]=2)[C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54289372HCID 54289372, compound

Product 1

HCID 18958954HCID 18958954, compoundYield 39.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 4-(2-methylimidazo[4,5-c]pyrid-1-yl)phenylacetate (750 mg, 2.54 mmol) and sodium hydroxide 160 mg, 4.0 mmol) in a mixture of ethanol (5 ml) and water (5 ml) was stirred at room temperature for 16 hours and evaporated. The residue was taken up in water, acidified with 2M hydrochloric acid to pH 4-5 and extracted into 1-butanol. The combined 1-butanol extracts were evaporated and the residue triturated with diethyl ether. The resulting solid was collected, washed with hexane and dried to give the title compound (267 mg, 39%) as a buff solid, m.p. 226°-230° C., which was characterised by its 1H-NMR spectrum. 1H-NMR (d6 -DMSO) δ=8.86(1H,s), 8.23(1H,d,J=8 Hz), 7.48(4H,s), 7.15(1H,d,J=8 Hz), 3.70(2H,s), 2.42(3H,s).

Workup

  1. customevaporated
  2. extractionextracted into 1-butanol
  3. customThe combined 1-butanol extracts were evaporated
  4. customthe residue triturated with diethyl ether
  5. customThe resulting solid was collected
  6. washwashed with hexane
  7. customdried

Sources & evidence

ORD record
ord-aac1e1ca85d446cbabbfe68e2a45ee2c
Source dataset
uspto-grants-1994_10
Patent number
US05358953

Reaction notes

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