2-Phenylacetophenone → HCID 56644284, compound

HRID 924642Notes

Reaction equation

HRID 924642 reaction equation
[C:1]1([C:7](=O)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([N+:28]([O-:30])=[O:29])[C:26]=1[OH:27])[CH:22]=O)[CH3:17].[CH3:31][C:32]1(C)[O:39]C(=O)CC(=O)O1.C([O-])(=O)C.[NH4+:45]>C(O)(=O)C>[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([CH:22]2[C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[NH:45][C:32](=[O:39])[CH2:31]2)[CH:24]=[C:25]([N+:28]([O-:30])=[O:29])[C:26]=1[OH:27])[CH3:17]

Participants

6

Reactant 4

HCID 99482-PhenylacetophenoneHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 517165Ammonium AcetateHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehyde

Product 1

HCID 56644284HCID 56644284, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1,2-diphenylethanone (150 mg, 0.76 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (194 mg, 0.92 mmol), meldrum's acid (132 mg, 0.92 mmol) and ammonium acetate (71 mg, 0.92 mmol) in acetic acid (5 mL) was refluxed overnight. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (EtOAc: PE=2:1) and prep-HPLC (0.1% TFA as additive) to afford Compound 1 as yellow solid (40 mg, yield: 13%). 1H NMR (DMSO-d6 300 MHz): δ 10.20 (s, 1H), 9.60 (s, 1H), 7.47 (d, J=3.0 Hz, 1H), 7.24-7.18 (m, 6H), 7.01-6.96 (m, 3H), 6.79 (d, J=8.1 Hz, 2H), 4.06 (q, J=6.0 Hz, 2H), 3.96 (d, J=5.1 Hz, 1H), 3.14-3.07 (m, 2H), 1.31 (t, J=7.2 Hz, 3H); MS (ESI): m/z 430.9 [M+H+].

Workup

  1. temperaturewas refluxed overnight
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (EtOAc: PE=2:1) and prep-HPLC (0.1% TFA as additive)

Sources & evidence

ORD record
ord-c3d3827c8e4b4d0d8867dbb8beb046de
Source dataset
uspto-grants-2016_03
Patent number
US09283213B2

Reaction notes

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