Dimethylformamide → Methyl 3-cyano-4-hydroxybenzoate

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Methylamine	HCID 6329	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
Reactant	Methyl 4-hydroxy-3-iodobenzoate	HCID 11346465	—
Product	Methyl 3-cyano-4-hydroxybenzoate	HCID 11769089	144.6%

Reaction Steps

To a solution of 11n DMF (158 mg, 0.41 mmol) were added amino acid 2 (100 mg, 0.52 mmol) and DIEA (272 μL, 0.16 mmol). The reaction was stirred for 14 h. Methylamine (2 M in THF, 0.4 mL) and HBTU (295 mg, 0.78 mmol) were then added. The reaction mixture was stirred for 5 h. The product was purified by RP-HPLC using a mixture of acetonitrile and H2O to give 3 (105 mg, 63%). LRMS (M+H+) m/z 401.1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07504413B2
Source dataset	uspto-grants-2009_03
ORD ID	ord-8ca2049a89034a2283d41632e74ea623
Source note	uspto-grants-2009_03