Trifluoroacetic acid → Picolinohydrazide

HRID 1774551Notes

Reaction equation

HRID 1774551 reaction equation
SC1C=C(C=CC=1)C(OC)=O.[N:12]1C(C)=[CH:16][CH:15]=[CH:14][C:13]=1C.C1N2CCN(CC2)C1.[NH2:28][NH2:29].[C:30](O)([C:32](F)(F)F)=[O:31]>>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:32]=1[C:30]([NH:28][NH2:29])=[O:31]

Participants

6

Reactant 5

HCID 6422Trifluoroacetic acidHCID 79372,6-LutidineHCID 9237DabcoHCID 9321HydrazineHCID 4362804Methyl 3-mercaptobenzoate

Product 1

HCID 255881Picolinohydrazide

Procedure

Compound 42 is prepared from methyl 3-mercaptobenzoate (41) and compound 42 under basic condition (e.g. 2-6-lutidine or DABCO). The ester functional group of compound 43 is then converted to hydrazide first (hydrazine reaction) and then Boc protecting group is deprotected under acidic condition (e.g. TFA) to afford compound 44.

Sources & evidence

ORD record
ord-00bf975c526f45cb96d14b7ac143e757
Source dataset
uspto-grants-2016_02
Patent number
US09260417B2

Reaction notes

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