Furfural → HCID 59053532, compound

HRID 1400285Notes

Reaction equation

HRID 1400285 reaction equation
[Cl-].[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[NH:13][CH2:14][CH2:15][NH3+:16].C([O-])([O-])=O.[K+].[K+].[O:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[CH:28]=O.[BH4-].[Na+]>CO.C(OCC)(=O)C>[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[NH:13][CH2:14][CH2:15][NH:16][CH2:28][C:24]1[O:23][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 7362FurfuralHCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 68152103HCID 68152103, compound

Product 1

HCID 59053532HCID 59053532, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[(1-chloronaphthalen-2-yl)amino]ethanaminium chloride (73 mg, 0.25 mmol) in 4 mL of MeOH, K2CO3 (104 mg, 0.75 mmol) was added. After 10 min, 21 μL (0.253 mmol) of furan-2-carbaldehyde were added. The resulting solution was stirred for 2 h at room temperature, added with sodium borohydride (10 mg, 0.275 mmol) and the reaction was allowed to stir for further 15 h at rt. The mixture was diluted with 10 mL of ethyl acetate and transferred to a separatory funnel. The organic layer was washed with water and dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (CH2Cl2/MeOH 95:5 plus 0.3% NH4OH) to afford N-(1-chloronaphthalen-2-yl)-N′-(furan-2-ylmethyl)ethane-1,2-diamine as a yellow oil (63% yield).

Workup

  1. stirringto stir for further 15 h at rt
  2. customtransferred to a separatory funnel
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography on silica gel (CH2Cl2/MeOH 95:5 plus 0.3% NH4OH)

Sources & evidence

ORD record
ord-157818601b964bfebaf8bd48451a9bdf
Source dataset
uspto-grants-2014_12
Patent number
US08906946B2

Reaction notes

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