3-Nitrobenzaldehyde → HCID 58906331, compound

HRID 1294730Notes

Reaction equation

[CH2:1]([N:3]([CH2:13][CH3:14])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8](I)=[CH:7][CH:6]=1)[CH3:2].[Li]CCCC.[N+:20]([C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH:26]=[O:27])([O-:22])=[O:21].[NH4+].[Cl-]>C1COCC1.C1(C)C=CC=CC=1.C1COCC1>[OH:27][CH:26]([C:25]1[CH:28]=[CH:29][CH:30]=[C:23]([N+:20]([O-:22])=[O:21])[CH:24]=1)[C:8]1[CH:9]=[CH:10][C:5]([C:4]([N:3]([CH2:13][CH3:14])[CH2:1][CH3:2])=[O:12])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

N,N-Diethyl-4-iodobenzamide (5.0 g, 16 mmol) was dissolved in THF (150 mL) and cooled to −78° C. under nitrogen atmosphere. n-BuLi (15 mL, 1.07 M solution in hexane, 16 mmol) was added dropwise during 10 min at −65 to −78° C. The solution was then canulated into 3-nitrobenzaldehyde (2.4 g, 16 mmol) in toluene/THF (approx. 1:1, 100 mL) at −78° C. NH4Cl (aq.) was added after 30 min. After concentration in vacuo, extraction with EtOAc/water, drying (MgSO4) and evaporation of the organic phase, the residue was purified by chromatography on silica (0-75% EtOAc/heptane) to give INTERMEDIATE 2 (2.6 g, 50%). 1H NMR (CDCl3) δ 1.0-1.3 (m, 6H), 3.2, 3.5 (2m, 4H), 5.90 (s, 1H), 7.30-7.40 (m, 4H), 7.50 (m, 1H), 7.70 (d, J=8 Hz, 1H), 8.12 (m, 1H), 8.28 (m, 1H).

Workup

concentrationAfter concentration
extractionin vacuo, extraction with EtOAc/water
customdrying
custom(MgSO4) and evaporation of the organic phase
customthe residue was purified by chromatography on silica (0-75% EtOAc/heptane)

Sources & evidence

ORD record: ord-a3238a19753546b68a7bae8c8a2490af
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07241764B2

Reaction notes

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