Sodium borohydride → HCID 19093003, compound

HRID 487730Notes

Reaction equation

HRID 487730 reaction equation
[BH4-].[Na+].[N+:3]([C:6]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[C:7]=1[CH:8]=[O:9])([O-:5])=[O:4]>>[OH:9][CH2:8][C:7]1[C:10]([O:18][CH3:19])=[C:11]([O:16][CH3:17])[C:12]([O:14][CH3:15])=[CH:13][C:6]=1[N+:3]([O-:5])=[O:4]

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 123200312,3,4-Trimethoxy-6-nitrobenzaldehyde

Product 1

HCID 19093003HCID 19093003, compoundYield 90.9%

Procedure

Sodium borohydride (4.44 g. 0.12 mol) was added portionwise to a suspension of 2-nitro-4,5,6-trimethoxybenzaldehyde (24.2 g, 0.1 mol) in 200 ml during 0.5 hours at 5-10 ° C. in an ice-bath. The mixture was stirred for an additional 10 minutes, and the excess of NaBH4 was destroyed by addition of acetic acid. The mixture was then concentrated in vacuo to dryness, and the solid residue was triturated with water. The solid was collected by filtration, washed with water and recrystallized from ethanol to give 22.1 g (90.9%) of 2-hydroxymethyl-1-nitro-3,4,5-trimethoxybenzene; mp 69-70° C. 1H-NMR (CDCl3): δ2.89 (1H, b, exchangeable, OH) 3.94, 3.96, and 3.97 (each 3H, s, 3×OMe), 4.78 (2h, s, CH2), 7.38 (1H, s, H-6). Analyses: Calculated for C10H13NO6 : C, 49.38; H, 5.39; N, 5.76. Found: C, 49.44; H, 5.43; N, 5.79.

Workup

  1. customthe excess of NaBH4 was destroyed by addition of acetic acid
  2. concentrationThe mixture was then concentrated in vacuo to dryness
  3. customthe solid residue was triturated with water
  4. filtrationThe solid was collected by filtration
  5. washwashed with water
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-1e295e59ac1742dd8da70bcd64456338
Source dataset
uspto-grants-1994_03
Patent number
US05296602

Reaction notes

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