Water → HCID 23326372, compound

HRID 1380280Notes

Reaction equation

HRID 1380280 reaction equation
[CH2:1]([NH:8][C:9]1[C:14]([N+:15]([O-])=O)=[C:13]([O:18][CH3:19])[CH:12]=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[N:23]#[C:24]Br>CO.[Pt]=O>[NH2:23][C:24]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]2[C:10]([O:20][CH3:21])=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[C:14]=2[N:15]=1

Participants

6

Reactant 3

HCID 962WaterHCID 10476Cyanogen BromideHCID 13648733HCID 13648733, compound

Product 1

HCID 23326372HCID 23326372, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

2-Benzylamino-3-nitro-1,4-dimethoxybenzene (10.0 g, 0.03 mole) is suspended in methanol and hydrogenated in the presence of platinum oxide catalyst at 50 psi for about twelve hours. After this time the solution changes color from red to colorless. The methanol is then removed in vacuo. To the residue is added approximately 250 ml water and 3.50 g (0.03 mole) of cyanogen bromide. The flask containing this mixture is stoppered, shaken, and stirred overnight at room temperature. After treatment with activated charcoal, the solution is filtered into excess 1N NaOH, causing the precipitation of the product. The amorphous white powder melts at 191°-193° C.

Workup

  1. customThe methanol is then removed in vacuo
  2. additionThe flask containing this mixture
  3. stirringstirred overnight at room temperature
  4. filtrationAfter treatment with activated charcoal, the solution is filtered into excess 1N NaOH
  5. customthe precipitation of the product

Sources & evidence

ORD record
ord-a794c9fab1954bd49d2a34658ce43b9b
Source dataset
uspto-grants-1986_04
Patent number
US04581349

Reaction notes

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