Hydrochloric Acid → HCID 51348807, compound

HRID 401060Notes

Reaction equation

HRID 401060 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](=O)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O[C:23]1[CH:30]=[C:29]([OH:31])[C:28]([N+:32]([O-:34])=[O:33])=[CH:27][C:24]=1[CH:25]=O)C.[NH2:35][C:36]([NH2:38])=[O:37].Cl.[CH3:40][CH2:41][OH:42]>>[CH2:41]([O:42][C:30]1[CH:23]=[C:24]([CH:25]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:11]([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)[NH:38][C:36](=[O:37])[NH:35]2)[CH:27]=[C:28]([N+:32]([O-:34])=[O:33])[C:29]=1[OH:31])[CH3:40]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 1176UreaHCID 27494642-Naphtylbenzyl ketone2×HCID 86669333HCID 86669333, compound

Product 1

HCID 51348807HCID 51348807, compoundYield 12.6%

Procedure

A mixture of 1-(naphthalen-2-yl)-2-phenylethanone (Intermediate 43) (260 mg, 1.06 mmol), -ethoxy-4-hydroxy-5-nitrobenzaldehyde (267.6 mg, 1.27 mmol), and urea (190.2 mg, 3.17 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 reduce pressure, and the residue was purified by column chromatography (EtOAc:MeOH=50:1) and preparative HPLC to afford Compound 85 as a yellow solid (64 mg, yield: 12.6%). 1H NMR (DMSO-d6 400 MHz): δ 10.12 (d, J=12.0 Hz, 1H), 8.65 (d, J=16.0 Hz, 1H), 7.67-7.81 (m, 3H), 7.30-7.46 (m, 5H), 6.99-7.18 (m, 2H), 6.58-6.73 (m, 5H), 5.14-5.35 (m, 1H), 3.90-3.96 (m, 2H), 1.16-1.22 (m, 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
  3. customthe residue was purified by column chromatography (EtOAc:MeOH=50:1) and preparative HPLC

Sources & evidence

ORD record
ord-7338b7555dc34f1f993616124a86cc88
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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