Formic Acid → HCID 58636821, compound

HRID 1158933Notes

Reaction equation

HRID 1158933 reaction equation
CC1(C)[O:22][C:6]2=[C:7]([CH3:21])[N:8]=[CH:9][C:10]([CH2:11][O:12][C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=3)=[C:5]2[CH2:4][O:3]1.C(O)=O>C1COCC1.O>[OH:22][C:6]1[C:5]([CH2:4][OH:3])=[C:10]([CH2:11][O:12][C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)[CH:9]=[N:8][C:7]=1[CH3:21]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 58636753HCID 58636753, compound

Product 1

HCID 58636821HCID 58636821, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-ylmethoxy)-benzonitrile (12) (3.10 g, 10 mmol) in THF (30 mL) was heated in a solution of 10% formic acid in water for 2 hours at 80° C. Upon evaporating the solvent, the crude product was washed with a mixture of ethyl acetate and hexane (1:2, 200 mL) to give 4-(5-hydroxy-4-hydroxymethyl-6-methyl-pyridin-3-ylmethoxy)-benzonitrile (13) (2.48 g, 92% yield).

Workup

  1. customUpon evaporating the solvent
  2. washthe crude product was washed with a mixture of ethyl acetate and hexane (1:2, 200 mL)

Sources & evidence

ORD record
ord-3ca2448a8aea49039475fef834d611a5
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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