5-Nitrofurfural → HCID 178496314, compound

HRID 845580Notes

Reaction equation

HRID 845580 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:29])=[C:5]([C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])[CH:6]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][OH:22])[CH:16]=2)[C:7]=1[C:8]([O:10][CH2:11][CH2:12][O:13][CH3:14])=[O:9].[N+:30]([C:33]1[O:37][C:36]([CH:38]=O)=[CH:35][CH:34]=1)([O-:32])=[O:31]>>[CH3:1][C:2]1[NH:3][C:4]([CH3:29])=[C:5]([C:23]([O:25][CH:26]([CH3:27])[CH3:28])=[O:24])[CH:6]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N:21](=[CH:38][C:36]3[O:37][C:33]([N+:30]([O-:32])=[O:31])=[CH:34][CH:35]=3)=[O:22])[CH:16]=2)[C:7]=1[C:8]([O:10][CH2:11][CH2:12][O:13][CH3:14])=[O:9]

Participants

3

Reactant 2

HCID 127745-NitrofurfuralHCID 14183058HCID 14183058, compound

Product 1

HCID 178496314HCID 178496314, compoundYield 81%

Procedure

The reaction of hydroxylamine 55 (0.80 g, 2 mmol) with 5-nitro-2-furaldehyde (65) (0.282 g, 2 mmol) afforded, after workup, a purple oil. The crude product was purified by flash chromatography with 1:1 ethyl acetate/hexane as the eluant to obtain 0.85 g (1.61 mmol, 81%) of 76 as a brown gum; IR (CH2Cl2) 3440, 1698, 1622, 1528, 1470, 1350, 1215, 1100, 1012, 810 cm-1 ; 1H NMR (CDCl3) δ 1.09 (d, J=6.2 Hz, 3H), 1.23 (d, J=6.2 Hz, 3H), 2.33 (s, 6H), 3.35 (s, 3H), 3.55-3.59 (m, 2H), 4.17-4.21 (m, 2H), 4.94 (septet, J=6.2 Hz, 1H), 5.09 (s, 1H), 6.20 (s, 1H), 7.34-8.29 (m, 7H); 13C NMR (CDCl3) δ 19.49, 19.59, 21.92, 22.18, 40.22, 58.85, 62.91, 67.36, 70.73, 103.11, 103.88, 113.84, 116.76, 118.98, 120.73, 122.43, 128.83, 131.37, 144.54, 145.28, 147.09, 149.47, 150.02, 151.63, 166.83, 167.31. Anal. Calcd for C26H29N3O9 : C, 59.20; H, 5.50. Found: C, 59.47; H, 5.74.

Workup

  1. customafforded
  2. customThe crude product was purified by flash chromatography with 1:1 ethyl acetate/hexane as the eluant

Sources & evidence

ORD record
ord-627d4f409b2242bf844ac42545f4a53d
Source dataset
uspto-grants-1988_07
Patent number
US04758669

Reaction notes

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