Hydrochloric Acid → HCID 9933608, compound

HRID 2228552Notes

Reaction equation

HRID 2228552 reaction equation
[NH2:1][C:2](=[N:31]O)[C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][CH:30]=1)[C:6]([NH:8][C:9]1[C:10]([NH:16][C:17](=[O:27])[C:18]2[CH:23]=[CH:22][C:21]([CH:24]([CH3:26])[CH3:25])=[CH:20][CH:19]=2)=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=1)=[O:7].CCO.[ClH:36]>[Pd].O>[ClH:36].[NH2:31][C:2](=[NH:1])[C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][CH:30]=1)[C:6]([NH:8][C:9]1[C:10]([NH:16][C:17](=[O:27])[C:18]2[CH:23]=[CH:22][C:21]([CH:24]([CH3:26])[CH3:25])=[CH:20][CH:19]=2)=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=1)=[O:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 54161665HCID 54161665, compound

Product 1

HCID 9933608HCID 9933608, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of N1-[3-(amino(hydroxyimino)methyl)benzoyl]N2-(4-isopropylbenzoyl)-4-hydroxy-1,2-benzenediamine (209 mg, 0.48 mmol), EtOH (5 mL), H2O (2.5 mL), 1N HCl (0.5 mL, 0.5 mmol), and 10% Pd/C (217 mg) was hydrogenated at 1 atm. for 14 h. The reaction was filtered through diatomaceous earth with hot methanolic washes. The filtrate was concentrated and the residue was resubjected to the hydrogenation conditions using 10% Pd/C (189 mg). After 6 h, the reaction mixture was filtered through diatomaceous earth with hot methanolic washes. The filtrate was concentrated to give the title compound as a solid (134 mg, 62%); NMR(300 MHz, DMSO-d6): δ10.27 (s, 1H), 9.89 (s, 1H), 9.45 (s, 2H), 9.14 (s, 2H), 8.42 (s, 1H), 8.23 (d, J=7.5, 1H), 7.94 (d, J=7.2, 1H), 7.86 (d, J=8.1, 2H), 7.73 (t, J=7.8, 1H), 7.28 (m, 4H), 6.65 (d, J=8.7, 1H), 2.90 (m, 1H), 1.19 (s, 3H), 1.17 (s, 3H); MS(FD): 399.2 (M—OH).

Workup

  1. filtrationThe reaction was filtered through diatomaceous earth with hot methanolic washes
  2. concentrationThe filtrate was concentrated
  3. waitAfter 6 h
  4. filtrationthe reaction mixture was filtered through diatomaceous earth with hot methanolic washes
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-be5b6829e8774ac5bd86e6d30720ada6
Source dataset
uspto-grants-2002_07
Patent number
US06417200B1

Reaction notes

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