Reaktion #1350558

Reaktionsgleichung

sodium borohydride

5-amino-2-methylphenol

pyrrole-2-carboxaldehyde

sodium acetate

→

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

Ausbeute 41.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

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
   Sonstigeonto crushed ice slurry (200 g)
5. 5
   Sonstigethe resulting precipitate was collected
6. 6
   Waschenwashed with cold water three times
7. 7
   Sonstigeair-dried

Vorschrift

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+).

Quelle