Hydrochloric Acid → HCID 51347780, compound

HRID 924797Notes

Reaction equation

HRID 924797 reaction equation
O=[C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[C:7]#[N:8].[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>C(O)C>[CH2:18]([O:20][C:21]1[CH:22]=[C:23]([CH:24]2[C:3]([C:4]3[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=3)[C:7]#[N:8])=[C:2]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=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 98593112-(3-CYANOPHENYL)ACETOPHENONE2×

Product 1

HCID 51347780HCID 51347780, compoundYield 13.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(2-oxo-2-phenylethyl)benzonitrile (Intermediate 11) (80 mg, 0.36 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (76 mg, 0.36 mmol), and urea (50 mg, 1.08 mmol) in 20 mL of ethanol was added 0.2 mL of concentrated HCl solution, and the mixture was stirred at reflux for 2 days. After the solvent was removed under reduced pressure, the residue was purified by thin layer chromatography (PE:EtOAc=1:2) to give Compound 29 (22 mg, yield 2.5%). 1H NMR (CD3OD 400 MHz): δ 7.45 (s, 1H), 7.27 (d, J=7.2 Hz, 1H), 7.21-7.18 (m, 5H), 7.12-7.05 (m, 3H), 6.98 (s, 1H), 5.20 (s, 1H), 3.97-3.94 (m, 2H), 1.30 (t, J=6.8 Hz, 3H); MS (ESI): m/z 457.2 [M+1]+.

Workup

  1. temperatureat reflux for 2 days
  2. customAfter the solvent was removed under reduced pressure
  3. customthe residue was purified by thin layer chromatography (PE:EtOAc=1:2)

Sources & evidence

ORD record
ord-75273ad3f61646768eeabb44e9643395
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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