HCID 18001130, compound → HCID 18001132, compound

HRID 969279Notes

Reaction equation

HRID 969279 reaction equation
[OH:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-])=O)[C:3]=1[NH:4][C:5](=[O:20])[C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:18][CH2:17][CH2:16][N:15]([CH3:19])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1.[H][H]>[C].[Pd].CO>[NH2:25][C:21]1[CH:22]=[CH:23][CH:24]=[C:2]([OH:1])[C:3]=1[NH:4][C:5](=[O:20])[C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH2:18][CH2:17][CH2:16][N:15]([CH3:19])[CH2:14][CH2:13]2)=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 18001130HCID 18001130, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 18001132HCID 18001132, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2.14 g of 2′-hydroxy-4-(4-methyl-1,4-diazepan-1-yl)-6′-nitrobenzanilide, 43 ml of methanol and 467 mg of 10% palladium-carbon (wetting rate: 54.2%) was stirred in a hydrogen atmosphere of atmospheric pressure at 30° C. until the absorption of hydrogen had stopped. The catalyst was filtered out and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography using chloroform-methanol (20:1 to 10:1) to give 1.61 g of 2′-amino-6′-hydroxy-4-(4-methyl-1,4-diazepan-1-yl)benzanilide.

Workup

  1. filtrationThe catalyst was filtered out
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-216210ac30ef476db4382d98b6df3bb3
Source dataset
uspto-grants-2007_12
Patent number
US07307074B2

Reaction notes

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