1-Hydroxybenzotriazole → Methyl 3-cyano-4-hydroxybenzoate

HRID 730374Notes

Reaction equation

HRID 730374 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1I.[CH3:13][N:14](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.Cl.CNOC.CCN(C(C)C)C(C)C>CN(C=O)C>[C:13]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[OH:1])[C:6]([O:8][CH3:9])=[O:7])#[N:14]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 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 295.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2 (1.49 g, 2.29 mmol), HBTU (1.3 g, 3.44 mmol), HOBt (530 mg, 3.44 mmol), and N,O-dimethylhydroxylamine HCl salt (340 mg, 3.44 mmol) in DMF (20 mL) was added DIEA (785 uL, 4.58 mmol). The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated. The resulting residue was purified using silica gel (Hexanes/EtOAc=1:3) to give pure compound 3 (1.20 g, 78%) as an off-white, foamy solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe resulting residue was purified

Sources & evidence

ORD record
ord-7aee4e25ee0b431780a2c64e304a49c6
Source dataset
uspto-grants-2009_09
Patent number
US07582668B2

Reaction notes

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