Hydrogen Peroxide → Ammonium Bicarbonate

HRID 130905

Reaction equation

HRID 130905 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[CH:7]=O)[CH3:2].[C:13]([O-:16])([O-:15])=[O:14].[K+].[K+].F[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1.[CH3:28][CH:29]([CH3:33])[CH2:30][CH2:31][NH2:32].[OH:34]O>CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:7][NH:32][CH2:31][CH2:30][CH:29]([CH3:33])[CH3:28])[CH:9]=[CH:10][C:11]=1[O:12][C:20]1[CH:27]=[CH:26][C:23]([C:24]([NH2:25])=[O:34])=[CH:22][CH:21]=1)[CH3:2].[C:13](=[O:14])([OH:16])[O-:15].[NH4+:25]

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 7894IsoamylamineHCID 8467EthylvanillinHCID 11430Potassium Carbonate2×HCID 145174-Fluorobenzonitrile

Product 2

HCID 14013Ammonium BicarbonateHCID 59729983HCID 59729983, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

Dissolve 3-ethoxy-4-hydroxy-benzaldehyde (2.57 g, 15.45 mmol) in DMF (20 mL), add K2CO3 (2.33 g, 16.86 mmol) and 4-fluorobenzonitrile (1.70 g, 14.05 mmol), heat the mixture at 130° C. overnight. Add water and extract the aqueous layer with EtOAc. Combine organic layers and dry over Na2SO4. Eliminate the solvent and purify by flash chromatography on silica gel (eluent: EtOAc/hexane 15/85) to get a mixture of two compounds (1.45 g). This mixture (240 mg) is submitted to the reductive amination conditions described for compound 1 (step 3) using 3-methyl-butylamine to obtain a mixture of two compounds which is subject to hydrolysis using hydrogen peroxide and potassium carbonate in the conditions described elsewhere in this document. This mixture is purified by flash chromatography (EtOAc and CH2Cl2/MeOH 10%) and then the title compound is isolated after HPLC (Column: XTerraMSC18 (5 um, 19×100 mm). Isocratic mode: 55/45 Ammonium bicarbonate-pH 9-/Acetonitrile. Flow: 10 mL/min).

Workup

  1. extractionAdd water and extract the aqueous layer with EtOAc
  2. dry with materialCombine organic layers and dry over Na2SO4
  3. custompurify by flash chromatography on silica gel (eluent: EtOAc/hexane 15/85)
  4. customto get
  5. customto obtain
  6. additiona mixture of two compounds which
  7. customis subject to hydrolysis
  8. customThis mixture is purified by flash chromatography (EtOAc and CH2Cl2/MeOH 10%)

Sources & evidence

ORD record
ord-cc0e8454054e4ccdb4c60b683943b774
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Linked notes

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