Hydrochloric Acid → HCID 66825924, compound

HRID 401097Notes

Reaction equation

HRID 401097 reaction equation
[C:1]1([CH2:7][C:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)=O)[CH:6]=[CH:5][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>C(O)C>[CH2:20]([O:22][C:23]1[CH:24]=[C:25]([CH:26]2[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:8]([C:10]3[CH:11]=[C:12]4[C:17](=[CH:18][CH:19]=3)[N:16]=[CH:15][CH:14]=[CH:13]4)[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 63095960HCID 63095960, compound2×

Product 1

HCID 66825924HCID 66825924, compoundYield 11.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-phenyl-1-(quinolin-6-yl)ethanone (Intermediate 67) (100 mg, 0.4 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (85 mg, 0.4 mmol) and urea (72 mg, 1.2 mmol) in 2 mL of ethanol was added 0.5 mL of conc. HCl and was stirred at reflux overnight. The mixture was cooled to room temperature and purified by preparative HPLC (20-50% acetonitrile+0.15% trifluoroacetic acid in water, over 15 min.), followed by column chromatography (PE: EtOAc=2:1-EtOAc:MeOH=10:1) to give Compound 132 (18 mg, yield 11.8%). 1H NMR (CD3OD 400 MHz): δ 8.84 (d, J=3.2 Hz, 1H), 8.30 (d, J=8.8 Hz, 1H), 7.94 (s, 1H), 7.86 (d, J=8.8 Hz, 1H), 7.66 (s, 1H), 7.59-7.52 (m, 2H), 7.19 (s, 1H), 7.06 (m, 3H), 6.95-6.94 (m, 2H), 5.45 (s, 1H), 4.13-4.05 (m, 2H), 1.41 (t, J=6.8 Hz, 3H); MS (ESI): m/z 483.3 [M+1]+.

Workup

  1. temperatureat reflux overnight
  2. custompurified by preparative HPLC (20-50% acetonitrile+0.15% trifluoroacetic acid in water, over 15 min.)

Sources & evidence

ORD record
ord-f99864e0f9ef47a499d092f7b41a144e
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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