Dichloromethane → 2,6-Dihydroxybenzonitrile

HRID 660621Notes

Reaction equation

HRID 660621 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:3]=1[CH:4]=O.S(O)(O)(=O)=O.[NH2:16]O.C(Cl)Cl.C([O-])(O)=O.[Na+]>O>[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:3]=1[C:4]#[N:16]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 159255Hydroxylamine, sulfate (1:1)HCID 516892Sodium BicarbonateHCID 102858012,6-Dihydroxybenzaldehyde

Product 1

HCID 937912,6-Dihydroxybenzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,6-dihydroxybenzaldehyde (300 mg, 2.17 mmol) and hydroxylamine sulfate (758 mg, 6.51 mmol) in water (30 mL) is stirred at RT for 45 min. Methylene chloride (60 mL) is added followed by NaHCO3 (911 mg, 10.85 mmol) and the mixture is stirred at RT for 30 min. The organic phase is separated and dried over sodium sulfate and the solvent removed under reduced pressure to give the title compound as a pale yellow solid.

Workup

  1. stirringthe mixture is stirred at RT for 30 min
  2. customThe organic phase is separated
  3. dry with materialdried over sodium sulfate
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-debdfd5d2d5f45438a483499e7fa3ccd
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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