4-Hydroxybenzaldehyde → HCID 2692494, compound

HRID 1291777Notes

Reaction equation

HRID 1291777 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([O:14][C:15](=[O:18])[NH:16][NH2:17])([CH3:13])([CH3:12])[CH3:11]>C(O)C>[C:10]([O:14][C:15]([NH:16][N:17]=[CH:6][C:5]1[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=1)=[O:18])([CH3:13])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 70091tert-Butyl carbazate

Product 1

HCID 2692494HCID 2692494, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Analogously to Example 4a, 14 g (106 mmol) of 4-hydroxybenzaldehyde and 14 g (117 mmol) of tert-butylcarbazate in 125 ml of ethanol are reacted to form 4-hydroxybenzaldehyde-tert-butoxycarbonylhydrazone. (19.8 g, 80%). 9.73 g thereof are hydrogenated in 200 ml of THF in the presence of 0.6 g of 5% palladium on carbon at 1 atm hydrogen pressure to yield the title compound, which is crystallised from hot methanol. 1H-NMR (200 MHz, CD3OD): 7.18 (d, J=8 Hz, 2H), 6.73 (d, J=8 Hz, 2H), 3.80 (s, 2H), 1.45 (s, 9H).

Sources & evidence

ORD record
ord-c79ef97584484b01a75ebfac981cf489
Source dataset
uspto-grants-1998_05
Patent number
US05753652

Reaction notes

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