Hydrochloric Acid → 2-Methyl-5-(2-nitro-4-[2-(3,4,5-trimethoxy-phenyl)-acetylamino]-phenyl)-furan-3-carboxylic acid

HRID 383595Notes

Reaction equation

HRID 383595 reaction equation
C[O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:31])[CH2:18][C:19]3[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=3)=[CH:12][C:11]=2[N+:32]([O-:34])=[O:33])[O:7][C:6]=1[CH3:35])=[O:4].[Li+].[OH-].Cl>C1COCC1.CO.CCOC(C)=O>[CH3:35][C:6]1[O:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:31])[CH2:18][C:19]3[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=3)=[CH:12][C:11]=2[N+:32]([O-:34])=[O:33])=[CH:9][C:5]=1[C:3]([OH:4])=[O:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 597857112-Methyl-5-{2-nitro-4-[2-(3,4,5-trimethoxy-phenyl)-acetylamino]-phenyl}-furan-3-carboxylic acid methyl ester

Product 1

HCID 597857142-Methyl-5-(2-nitro-4-[2-(3,4,5-trimethoxy-phenyl)-acetylamino]-phenyl)-furan-3-carboxylic acidYield 74.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 2-Methyl-5-{2-nitro-4-[2-(3,4,5-trimethoxy-phenyl)-acetylamino]-phenyl}-furan-3-carboxylic acid methyl ester (59) (50 mg, 0.10 mmol) in THF (1.0 mL) and MeOH (0.5 mL) at rt and add 1M aqu LiOH (525 μL, 0.52 mmol). Stir the reaction mixture for 17 h at rt. Add dropwise 1M aqu. HCl (5804, 0.58 mmol) and extract the mixture with EtOAc (3 times), wash the combined organic layer with brine and dry it with Na2SO4. Purify the obtained crude product by preparative TLC (silica gel, EtOAc/MeOH 9+1) to obtain 2-Methyl-5-{2-nitro-4-[2-(3,4,5-trimethoxy-phenyl)-acetylamino]-phenyl}-furan-3-carboxylic acid (60) (35 mg, 71%) as a brown sticky solid. 1H NMR (400 MHz, CDCl3): 2.61 (s, 3H); 3.70 (s, 2H); 3.86 (s, 3H); 3.87 (s, 6H); 6.51 (s, 2H); 6.85 (s, 1H); 7.29 (br.s, 1H); 7.58 (d, 1H, J=8.6 Hz); 7.62 (dd, 1H, J1=9.0 Hz, J2=2.2 Hz); 7.98 (d, 1H, J=2.0 Hz).

Workup

  1. additionAdd dropwise 1M aqu
  2. washwash the combined organic layer with brine
  3. dry with materialdry it with Na2SO4
  4. customPurify the
  5. customobtained crude product by preparative TLC (silica gel, EtOAc/MeOH 9+1)

Sources & evidence

ORD record
ord-4acc6ffba1174eb6b7b7a411aa217614
Source dataset
uspto-grants-2013_02
Patent number
US08367677B2

Reaction notes

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