Pyrrole-2-carboxaldehyde → HCID 11390060, compound

HRID 1263376Notes

Reaction equation

HRID 1263376 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([OH:8])[CH:7]=1.[NH:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[CH:15]=O.C([O-])(=O)C.[Na+].[BH4-].[Na+]>CO>[CH3:9][C:5]1[CH:4]=[CH:3][C:2]([NH:1][CH2:15][C:11]2[NH:10][CH:14]=[CH:13][CH:12]=2)=[CH:7][C:6]=1[OH:8]

Participants

6

Reactant 4

HCID 13854Pyrrole-2-carboxaldehydeHCID 178185-Amino-2-methylphenolHCID 517045Sodium AcetateHCID 4311764Sodium borohydride

Product 1

HCID 11390060HCID 11390060, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 5-amino-2-methylphenol (9.84 g, 80 mmole) in methanol (100 mL) at 4° C. was added pyrrole-2-carboxaldehyde (11.41 g, 120 mmole) and sodium acetate (13.13 g, 160 mmole). The reaction mixture was stirred for 15 minutes and sodium borohydride (3.78 g, 100 mmole) was added portionwise over 1 hour at 4° C. After the addition was complete, the reaction was allowed to stir for an additional 3 hours. The reaction mixture was poured onto crushed ice slurry (200 g) and the resulting precipitate was collected and washed with cold water three times and air-dried to afford 2-methyl-5-[(1H-pyrrol-2-yl-methyl)amino]phenol (6.62 g, 41% yield): mp 115.4-116.8° C.; 1HNMR (400 MHz, DMSO-d6) δ 1.94 (s, 3H), 4.03 (d, 2H, J=5.6 Hz), 5.37 (t, 1H, J=5.6 Hz), 5.90 (m, 2H), 6.01 (dd, 1H, J=2.2, 8.0 Hz), 6.12 (d, 1H, J=2.1 Hz), 6.61 (m, 1H), 6.70 (d, 1H, J=8.1 Hz), 8.77 (s, 1H), 10.64 (s, 1H); MS m/z 202 (M+).

Workup

  1. additionAfter the addition
  2. stirringto stir for an additional 3 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-c2b90314c2154634a66c7fbad5a7c73e
Source dataset
uspto-grants-2003_04
Patent number
US06540793B1

Reaction notes

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