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Water → 5-(2-(4-Fluorophenyl)-3-(methylcarbamoyl)-6-nitrobenzofuran-5-yl)-2-methoxybenzoic acid

HRID 1892565
Notes
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Reaction equation

HRID 1892565 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[C:18]([C:24]4[CH:25]=[CH:26][C:27]([O:34][CH3:35])=[C:28]([CH:33]=4)[C:29]([O:31]C)=[O:30])=[CH:17][C:11]=3[C:12]=2[C:13](=[O:16])[NH:14][CH3:15])=[CH:4][CH:3]=1.O.[OH-].[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[C:18]([C:24]4[CH:25]=[CH:26][C:27]([O:34][CH3:35])=[C:28]([CH:33]=4)[C:29]([OH:31])=[O:30])=[CH:17][C:11]=3[C:12]=2[C:13](=[O:16])[NH:14][CH3:15])=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67957912Methyl 5-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-nitrobenzofuran-5-yl)-2-methoxybenzoate

Product 1

HCID 679582765-(2-(4-Fluorophenyl)-3-(methylcarbamoyl)-6-nitrobenzofuran-5-yl)-2-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 5-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-nitrobenzofuran-5-yl)-2-methoxybenzoate (200 mg, 0.418 mmol) in THF (12 mL)/water (4.0 mL) at room temperature was added sodium hydroxide (1.045 mL, 2.090 mmol). The reaction mixture was heated to 50° C. and maintained at the same temperature for overnight. The reaction mixture was concentrated under vacuum to remove the solvent. The residue was diluted with water, acidified with 1.5 N HCl. The solid obtained was filtered and dried under suction. Yield: 175 mg (86%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.81 (br. s, 1H). 8.58 (q, J=4.52 Hz, 1H), 8.49 (s, 1H), 8.08-8.02 (m, 2H), 7.70 (s, 1H), 7.66 (d, J=2.51 Hz, 1H), 7.53 (dd, J=8.66, 2.38 Hz, 1H), 7.49-7.42 (m, 2H), 7.25 (s, 1H), 3.89 (s, 3H), 2.85 (d, J=4.77 Hz, 3H).

Workup

  1. temperaturemaintained at the same temperature for overnight
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customto remove the solvent
  4. additionThe residue was diluted with water
  5. customThe solid obtained
  6. filtrationwas filtered
  7. customdried under suction

Sources & evidence

ORD record
ord-4f20831dc14f4a0aa1a16e800ef9ff7e
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08507683B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes