Dimethylformamide → Methyl 3-cyano-4-hydroxybenzoate

HRID 1621255Notes

Reaction equation

HRID 1621255 reaction equation
[CH3:1][N:2](C=O)C.[OH:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][C:8]=1I.CCN(C(C)C)C(C)C.CN.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[C:1]([C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:7]=1[OH:6])[C:11]([O:13][CH3:14])=[O:12])#[N:2]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11346465Methyl 4-hydroxy-3-iodobenzoate

Product 1

HCID 11769089Methyl 3-cyano-4-hydroxybenzoateYield 144.6%

Procedure

To a solution of 1 in 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.

Workup

  1. stirringThe reaction mixture was stirred for 5 h
  2. customThe product was purified by RP-HPLC
  3. additiona mixture of acetonitrile and H2O

Sources & evidence

ORD record
ord-6ef865321e014118a6f05f2baa9f9a0b
Source dataset
uspto-grants-2014_07
Patent number
US08772507B2

Reaction notes

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