Carbon Dioxide → HCID 68698185, compound

HRID 2236781Notes

Reaction equation

HRID 2236781 reaction equation
CO[N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[C:7]([OH:14])[CH:6]=1.C(=O)=O.[ClH:18].[H][H]>C(O)C.O1CCCC1.[Pd]>[ClH:18].[ClH:18].[NH2:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][NH2:3])=[CH:6][C:7]=1[OH:14]

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 72250763HCID 72250763, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 68698185HCID 68698185, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-hydroxy-4-nitrobenzaldehyde O-methyloxime (5.9 g, 30 mmol) in ethanol (100 mL) and tetrahydrofuran (100 mL) is degassed with solid carbon dioxide, then charged with 10% palladium on carbon (500 mg) and concentrated hydrochloric acid (5.5 mL). The mixture is shaken under 50 psi hydrogen gas until consumption of hydrogen had ceased. The mixture is then filtered through a pad of diatomaceous earth, and the filtrate is concentrated under reduced pressure to give 2-amino-5-(aminomethyl)phenol dihydrochloride (6.1 g, 97%).

Workup

  1. filtrationThe mixture is then filtered through a pad of diatomaceous earth
  2. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-8da476735ecf48cfbdaf4d4b4d6cf3a4
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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