Diazomethane → HCID 15662885, compound

HRID 487729Notes

Reaction equation

HRID 487729 reaction equation
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[C:5]([O:12][CH3:13])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[N+](=[CH2:19])=[N-]>CCOCC>[N+:14]([C:3]1[CH:4]=[C:5]([O:12][CH3:13])[C:6]([O:10][CH3:11])=[C:7]([O:8][CH3:9])[C:2]=1[O:1][CH3:19])([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 15662884HCID 15662884, compound

Product 1

HCID 15662885HCID 15662885, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-Hydroxy-2-nitro-4,5,6-trimethoxybenzene (4.58 g, 0.02 mol) was treated with diazomethane (prepared from 1-methyl-3-nitro-1-nitrosoguanidine, 5.88 g, 0.04 mol) in ether (300 ml) for 4 hours at room temperature. The reaction mixture was evaporated in vacuo to dryness, and the residue was chromatographed on a silica gel column (3×40 cm) using hexane/ethyl acetate (9:1) as the eluent. 1-Nitro-2,3,4,5-tetramethoxybenzene was obtained as syrup, 3.45 g (71%). 1NMR (CDCl3): δ3.80, 3.94, 3.96, and 3.98 (each 3H, s, 4×OMe), 7.18 (1H, s, H-6). Analyses: Calculated for C10H13NO6 : C, 49.38; H, 5.39; N, 5.76. Found: C, 49.14; H, 5.53; N, 5.75.

Workup

  1. customThe reaction mixture was evaporated in vacuo to dryness
  2. customthe residue was chromatographed on a silica gel column (3×40 cm)

Sources & evidence

ORD record
ord-e6203f0fb17c45c1854474c0d8a060c7
Source dataset
uspto-grants-1994_03
Patent number
US05296602

Reaction notes

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