Sodium borohydride → (10-Methylaminomethyl-anthracen-9-yl)-methanol

HRID 429708

Reaction equation

HRID 429708 reaction equation
[OH:1][CH2:2][C:3]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]=[N:18][CH3:19])=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[CH:8]2.[BH4-].[Na+]>C(O)(C)C>[OH:1][CH2:2][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10]([CH2:17][NH:18][CH3:19])=[C:11]2[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 2266220010-(Hydroxymethyl)-9-((methylimino)methyl)anthracene

Product 1

HCID 22353076(10-Methylaminomethyl-anthracen-9-yl)-methanolYield 86%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

10-(hydroxymethyl)-9-((methylimino)methyl)anthracene (1.00 g, 4.0 mmol) was slurried in 25 mL isopropanol. NaBH4 (0.454 g, 12.0 mmol) was added as a solid and the solution was stirred at room temperature for 72 h. The mixture was filtered on a sintered-glass frit and the solvent was removed under reduced pressure to yield 10 as a bright yellow powder (0.853 g, 86% yield): 1H NMR (300.13 MHz, CD3OD) δ2.55 (s, 3H), 4.64 (s, 2H), 5.56 (s, 2H), 7.55 (m, 4H), 8.38 (m, 2H), 8.50 (m, 2H); 13C-{1H} NMR (75.4 MHz, CD3OD) δ133.4, 133.0, 131.6, 131.5, 126.9, 126.7, 126.2, 125.7, 57.2, 47.9, 36.5.

Workup

  1. filtrationThe mixture was filtered on a sintered-glass frit
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-89c85c7d978d426693663479677aa049
Source dataset
uspto-grants-2001_11
Patent number
US06319540B1

Linked notes

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