Methane → HCID 19610492, compound

HRID 962866Notes

Reaction equation

HRID 962866 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:29]=[CH:28][C:13]([C:14]([NH:16][NH:17]C(OCC2C=CC=CC=2)=O)=[O:15])=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H].C>CO.[Pd]>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([NH:16][NH2:17])=[O:15])=[CH:28][CH:29]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 297MethaneHCID 19610537HCID 19610537, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19610492HCID 19610492, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of the product of step (a) (5.7 g) in methanol (120 ml) was hydrogenolysed over 10% palladium on carbon (0.5 g) until hydrogen uptake ceased (1 hour). Activated charcoal was added and the mixture was stirred, filtered through diatomaceous earth and concentrated to give 4-(t-butoxycarbonylaminomethyl)benzoylhydrazine (3.6 g) as a colourless solid; m.p. (from toluene) 114°-116° C.; NMR Spectrum 1.4 (9H, s); 3.2-4.0 (2H, br s); 4.2 (2H, s); 7.3 (2H, d); 7.4 (1H, t); 7.8 (2H, d); 9.7 (1H, s).

Workup

  1. custom(1 hour)
  2. filtrationfiltered through diatomaceous earth
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ffb1a8a52ea948bba82b7060239f0cf5
Source dataset
uspto-grants-1998_06
Patent number
US05760057

Reaction notes

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