Reaction #1350558

Reaction equation

sodium borohydride

5-amino-2-methylphenol

pyrrole-2-carboxaldehyde

sodium acetate

→

2-methyl-5-[(1H-pyrrol-2-yl-methyl)amino]phenol

Yield 41.0%

Solvents

methanol

Conditions

Workup

1. 1
   workup.ADDITIONAfter the addition
2. 2
   workup.STIRRINGto stir for an additional 3 hours
3. 3
   workup.ADDITIONThe reaction mixture was poured
4. 4
   Otheronto crushed ice slurry (200 g)
5. 5
   Otherthe resulting precipitate was collected
6. 6
   Washwashed with cold water three times
7. 7
   Otherair-dried

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+).

Source