Nitrogen → HCID 11299824, compound

HRID 480571Notes

Reaction equation

HRID 480571 reaction equation
N#N.[N+:3]([C:6]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=[O:9])([O-:5])=[O:4].[N+:16]([CH2:19][CH3:20])([O-:18])=[O:17].[F-].[K+]>O.C(O)(C)C>[N+:3]([C:6]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]([OH:9])[CH:19]([N+:16]([O-:18])=[O:17])[CH3:20])([O-:5])=[O:4]

Participants

7

Reactant 4

HCID 947NitrogenHCID 6587NitroethaneHCID 988673-Methoxy-2-nitrobenzaldehydeHCID 522689Potassium Fluoride

Product 1

HCID 11299824HCID 11299824, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent2×

Procedure

To a 2 L round-bottomed flask equipped with a magnetic stirrer and a N2 bubbler were added 2-nitro-3-methoxybenzaldehyde (125.7 g, 0.6939 mol), nitroethane (73 g, 0.97 mol), 18-C-6 (18 g), isopropanol (420 mL) and KF (20 g). The mixture was stirred at RT for 16 h. The solvent was removed under vacuum to give an oil. Isopropanol (100 mL) and water (250 mL) were added. The mixture was placed under vacuum to give a slurry. The slurry was stirred for 1 h and filtered. The cake was washed with water (4×100 mL) and dried to give 1-(2-nitro-3-methoxyphenyl)-2-nitropropanol as a diastereomeric mixture in a ratio of 3:2 (170.3 g, 96% yield). 1H NMR for major isomer (CDCl3) δ1.38 (d, J=6.9 Hz, 3H), 2.94 (s, 1H), 3.92 (s, 3H), 4.90 (m, 1H), 5.08 (d, J=8.6 Hz, 1H), 7.05-7.52 (m, 3H). 1H NMR for minor isomer (CDCl3) δ1.55 (d, J=6.9 Hz, 3H), 2.94 (s, 1H), 4.80 (m, 1H), 5.46 (d, J=3.0 Hz), 7.05-7.52 (m, 3H).

Workup

  1. customTo a 2 L round-bottomed flask equipped with a magnetic stirrer
  2. customThe solvent was removed under vacuum
  3. customto give an oil
  4. customto give a slurry
  5. stirringThe slurry was stirred for 1 h
  6. filtrationfiltered
  7. washThe cake was washed with water (4×100 mL)
  8. customdried

Sources & evidence

ORD record
ord-c40a2ffac5e04c37bbb4af0aa797243b
Source dataset
uspto-grants-2003_11
Patent number
US06653304B2

Reaction notes

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