Acetic Acid → HCID 67297269, compound

HRID 215834Notes

Reaction equation

HRID 215834 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[C:16]([CH3:17])=[CH:15][C:14]([N+:18]([O-])=O)=[CH:13][N:12]=2)=[CH:6][CH:5]=1.C(O)(=O)C>CO.[Zn]>[NH2:18][C:14]1[CH:15]=[C:16]([CH3:17])[C:11]([O:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([O:2][CH3:1])=[O:21])=[CH:9][CH:8]=2)=[N:12][CH:13]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 65019042HCID 65019042, compound

Product 1

HCID 67297269HCID 67297269, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 4-(3-methyl-5-nitro-pyridin-2-yloxy)-benzoic acid methyl ester (0.43 g, 1.49 mmol) from the previous step and zinc dust (0.932 g, 14.2 mmol) in methanol (15 ml) was added dropwise acetic acid (0.32 ml, 5.12 mmol). The mixture was stirred for 1 h at room temperature and filtered through a thin silica pad to remove inorganics. The filtrate was concentrated at reduced pressure to dryness to provide methyl 4-(5-amino-3-methylpyridin-2-yloxy)benzoate (0.346 g, 90% yield).

Workup

  1. filtrationfiltered through a thin silica pad
  2. customto remove inorganics
  3. concentrationThe filtrate was concentrated at reduced pressure to dryness

Sources & evidence

ORD record
ord-ae47a9d2e9d149db9d31afc64524d2be
Source dataset
uspto-grants-2012_06
Patent number
US08193192B2

Reaction notes

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