4-Methylbenzaldehyde → HCID 86592489, compound

HRID 968832Notes

Reaction equation

HRID 968832 reaction equation
[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])(=[O:4])[NH:2][NH2:3].[CH3:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1>O.C(O)(C)C.[Pd]>[CH3:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][N:2]([C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[NH2:3])=[CH:13][CH:12]=1

Participants

6

Reactant 2

HCID 77254-MethylbenzaldehydeHCID 70091tert-Butyl carbazate

Product 1

HCID 86592489HCID 86592489, compoundYield 88.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent7×

Conditions

Temperature
35 °C

Procedure

To a 10-gal stainless steel autoclave containing isopropanol (10 L) under nitrogen was charged t-butyl carbazate (1.25 kg, 9.46 mol)followed by isopropanol (2 L). The contents were stirred and heated at 35° C. for 30 min, then 4-methylbenzaldehyde (1.142 kg, 9.51 mol) was added, followed by isopropanol (0.3 L). The contents were heated to 45° C., and a slurry of 5% Pd/C (0.3 kg) in water (0.3 L) and isopropanol (4 L) was added, followed by rinses of isopropanol (2×1 L). The contents were hydrogenated at 40 psig and 45° C. for 4 h, then a second charge of 5% Pd/C (0.3 kg) in water (0.3 L) and isopropanol (4 L) was added, followed by rinses of isopropanol (2×1 L). Hydrogenation was continued at 40 psig and 45° C. for 14 h, at which the reaction was determined to be complete by HPLC. The contents were then cooled to 15° C. and filtered, and the filter cake rinsed with isopropanol (15 L). The filtrate was concentrated in vacuo to afford the title compound (1.97 kg, 88.2%) as a 33.8 wt-% solution in isopropanol.

Workup

  1. temperatureThe contents were heated to 45° C.
  2. additionwas added
  3. waitHydrogenation was continued at 40 psig and 45° C. for 14 h, at which
  4. temperatureThe contents were then cooled to 15° C.
  5. filtrationfiltered
  6. washthe filter cake rinsed with isopropanol (15 L)
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b43eb4c283044522b8baf95dddca19ff
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

Loading…