Hydrochloric Acid → HCID 66825735, compound

HRID 924843Notes

Reaction equation

HRID 924843 reaction equation
[C:1]1([C:11](=O)[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:20]([O:22][C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([N+:32]([O-:34])=[O:33])[C:30]=1[OH:31])[CH:26]=O)[CH3:21].[NH2:35][C:36]([NH2:38])=[O:37].Cl>CCO>[CH2:20]([O:22][C:23]1[CH:24]=[C:25]([CH:26]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:11]([C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)[NH:38][C:36](=[O:37])[NH:35]2)[CH:28]=[C:29]([N+:32]([O-:34])=[O:33])[C:30]=1[OH:31])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehydeHCID 2749463Ethanone, 1-(1-naphthalenyl)-2-phenyl-2×

Product 1

HCID 66825735HCID 66825735, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 1-(naphthalen-1-yl)-2-phenylethanone (Intermediate 41) (250 mg, 1.02 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (257.3 mg, 1.22 mmol), and urea (182.9 mg, 3.05 mmol) in anhydrous EtOH (5 mL) was added concentrated HCl solution (0.2 mL), and the reaction mixture was refluxed for 14 hours. The reaction mixture was concentrated under reduced pressure, and purified by column chromatography and preparative HPLC to afford Compound 81 as a yellow solid (89 mg, yield: 18.1%). 1H NMR (DMSO-d6 400 MHz): δ 10.30 (s, 1H), 8.84 (s, 1H), 6.49-7.89 (m, 8H), 6.87-7.23 (m, 7H), 5.26 (d, J=2.8 Hz, 1H), 4.02-4.11 (m, 2H), 1.32-1.36 (t, J=6.8 Hz, 3H); MS (ESI): m/z 482.1 [M+1]+.

Workup

  1. temperaturethe reaction mixture was refluxed for 14 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified by column chromatography and preparative HPLC

Sources & evidence

ORD record
ord-af24227fa3684edb9b1a01a441428555
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

Loading…