Ethyl 4-azido-2,6-bis(trifluoromethyl)-3-pyridinecarboxylate → Ethyl 4-amino-2,6-bis(trifluoromethyl)-3-pyridinecarboxylate

HRID 542122Notes

Reaction equation

HRID 542122 reaction equation
[N:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[N:7]=[C:6]([C:14]([F:17])([F:16])[F:15])[C:5]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N+]=[N-].[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[CH:9]=[C:8]([C:10]([F:11])([F:12])[F:13])[N:7]=[C:6]([C:14]([F:17])([F:15])[F:16])[C:5]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 2

HCID 13882885Ethyl 4-azido-2,6-bis(trifluoromethyl)-3-pyridinecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 13882886Ethyl 4-amino-2,6-bis(trifluoromethyl)-3-pyridinecarboxylateYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2.0 g (0.00611 mol) of product of Example 27, 100 mg of 10% Pd-C and 20 ml of ethanol was hydrogenated with 30 lbs. hydrogen pressure for three hours and filtered. The filtrate was concentrated. The residual oil (1.7 g) was triturated with petroleum ether and filtered to give 1.5 g (87%) of product as a white powder; mp 43°-45° C.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customThe residual oil (1.7 g) was triturated with petroleum ether
  4. filtrationfiltered

Sources & evidence

ORD record
ord-c8afd44ffad74c0890d632f70edc9835
Source dataset
uspto-grants-1987_04
Patent number
US04655816

Reaction notes

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