2-Thiophenecarboxaldehyde → HCID 69540551, compound

HRID 1531606Notes

Reaction equation

HRID 1531606 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([OH:8])[CH:7]=1.[S: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[S:10][CH:14]=[CH:13][CH:12]=2)[CH3:17])=[CH:7][C:6]=1[OH:8]

Participants

6

Reactant 4

HCID 73642-ThiophenecarboxaldehydeHCID 178185-Amino-2-methylphenolHCID 517045Sodium AcetateHCID 4311764Sodium borohydride

Product 1

HCID 69540551HCID 69540551, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-amino-2-methylphenol (12.30 g, 100 mmole) in methanol (100 mL) at 4° C. was added 2-thiophenecarboxaldehyde (16.82 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-(thiophen-2-yl-methylamino)phenol (7.12 g, 32% yield): mp 30.8-132.6° C.; 1HNMR (400 MHz, DMSO-d6) δ 1.94 (s, 3H), 4.34 (d, 2H, J=6.0 Hz) 5.91 (t, 1H, J=6.1 Hz), 6.00 (dd, 1H, J=2.3, 8.0 Hz), 6.11 (d, 1H, J=2.2 Hz), 6.70 (d, 1H, J=8.1 Hz), 6.95 (dd, 1H, J=3.5, 5.0 Hz), 7.00 (dd, 1H, J=0.8, 3.4 Hz), 7.34 (dd, 1H, J=1.0, 5.0 Hz), 8.79 (s, 1 H); MS m/z 219 (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-76a4881a6be743e49a36099189af981b
Source dataset
uspto-grants-2001_03
Patent number
US06200353B1

Reaction notes

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