Hydrochloric Acid → HCID 51347479, compound

HRID 400998Notes

Reaction equation

HRID 400998 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9](=O)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:7][CH:8]=1.[CH2:18]([O:20][C:21]1[CH:22]=[C:23]([CH:26]=[C:27]([N+:30]([O-:32])=[O:31])[C:28]=1[OH:29])[CH:24]=O)[CH3:19].[NH2:33][C:34]([NH2:36])=[O:35].Cl>CCO>[CH2:18]([O:20][C:21]1[CH:22]=[C:23]([CH:24]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[NH:36][C:34](=[O:35])[NH:33]2)[CH:26]=[C:27]([N+:30]([O-:32])=[O:31])[C:28]=1[OH:29])[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehydeHCID 27596153'-Methoxy-2-phenylacetophenone

Product 1

HCID 51347479HCID 51347479, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(3-methoxyphenyl)-2-phenylethanone (100 mg, 0.44 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (72 mg, 0.34 mmol), urea (80 mg, 1.33 mmol), and concentrated HCl solution (0.04 mL, 0.44 mmol) in EtOH (5 mL) was refluxed overnight. The mixture was evaporated in vacuo and the residue was purified by preparative HPLC to give Compound 15 (42.57 mg, yield 21%). 1H NMR (DMSO-d6 400 MHz): δ 10.29 (s, 1H), 8.72 (s, 1H), 7.54 (s, 1H), 7.44 (s, 1H), 7.18-7.12 (m, 2H), 7.08-7.02 (m, 3H), 6.86-6.81 (m, 3H), 6.77-6.74 (m, 2H), 5.20 (d, J=2.8 Hz, 1H), 4.05 (q, J=6.8 Hz, 2H), 3.63 (s, 3H), 1.33 (t, J=6.8 Hz, 3H); MS (ESI): m/z 462.1 [M+1]+.

Workup

  1. temperaturewas refluxed overnight
  2. customThe mixture was evaporated in vacuo
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-75d39d6a95d945f7820f4504573c3af1
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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