Furfural → HCID 69540568, compound

HRID 1263377Notes

Reaction equation

HRID 1263377 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([OH:8])[CH:7]=1.[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1C=O.[C:17]([O-])(=O)C.[Na+].[BH4-].[Na+]>CO>[CH3:9][C:5]1[CH:4]=[CH:3][C:2]([N:1]([C:11]2[O:10][CH:14]=[CH:13][CH:12]=2)[CH3:17])=[CH:7][C:6]=1[OH:8]

Participants

6

Reactant 4

HCID 7362FurfuralHCID 178185-Amino-2-methylphenolHCID 517045Sodium AcetateHCID 4311764Sodium borohydride

Product 1

HCID 69540568HCID 69540568, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 5-amino-2-methylphenol (12.30 g, 100 mmole) in methanol (100 mL) at 4° C. was added 2-furaldehyde (14.41 g, 150 mmole) and sodium acetate (16.41 g, 200 mmole). The reaction mixture was stirred for 15 minutes and sodium borohydride (4.73 g, 125 mmole) was added portionwise over 1 hour at 4° C. After the addition was complete, the reaction was allowed to stir for an additional 1.5 hours. The reaction mixture was poured onto crushed ice slurry (200 g) and the resulting precipitate was collected, washed with cold water three times and air-dried to afford 2-methyl-5-(furan-2-yl-methylamino)phenol (16.86 g, 83% yield): mp 126.8-128.5° C.; 1HNMR (400 MHz, DMSO-d6) δ 1.94 (s, 3H), 4.12 (d, 2H, J=6.1 Hz), 5.71 (t, 1H, J=6.1 Hz), 6.00 (dd, 1H, J=2.3, 8.0 Hz), 6.11 (d, 1H, J=2.2 Hz), 6.22 (d, 1H, J=3.0 Hz), 6.36 (m, 1H), 6.70 (d, 1H, J=8.1 Hz), 7.54 (t, 1H, J=0.8 Hz), 8.79 (s, 1H); MS m/z 203 (M+).

Workup

  1. additionAfter the addition
  2. stirringto stir for an additional 1.5 hours
  3. additionThe reaction mixture was poured
  4. customonto crushed ice slurry (200 g)
  5. customthe resulting precipitate was collected
  6. washwashed with cold water three times
  7. customair-dried

Sources & evidence

ORD record
ord-a71e006aeb984d1b85777373029e8dc1
Source dataset
uspto-grants-2003_04
Patent number
US06540793B1

Reaction notes

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