Acetaldehyde → 81244-91-9

HRID 1732588Notes

Reaction equation

HRID 1732588 reaction equation
[CH:1]1[C:9]2[C@H:10]3[O:15][CH2:14][CH2:13][NH:12][C@@H:11]3[CH2:16][C:7]3[C:8]=2[C:4]([NH:5][CH:6]=3)=[CH:3][CH:2]=1.[CH:17](=O)[CH3:18]>[Pd].C(O)C>[CH2:17]([N:12]1[C@@H:11]2[CH2:16][C:7]3[C:8]4[C:4]([NH:5][CH:6]=3)=[CH:3][CH:2]=[CH:1][C:9]=4[C@H:10]2[O:15][CH2:14][CH2:13]1)[CH3:18]

Participants

5

Reactant 2

HCID 177AcetaldehydeHCID 22813385HCID 22813385, compound

Product 1

HCID 1425483081244-91-9Yield 58.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of trans-4,6,6a,8,9,10a-hexahydro-7H-indolo-[3,4 gh]-[1,4]-benzoxazine (650 mg, 0.03 m) acetaldehyde (260 mg, 0.006 m) and Pd/c (10%, 700 mg) in abs. ethanol (50 ml) is hydrogenated at room temperature for 4 hours. The catalyst is removed by filtration, and the solvent is removed under reduced pressure (20 mm). The oil is recrystallized from methanol to yield 430 mg of trans 4,6,6a,8,9,10a-hexahydro-7-ethyl-7H-indolo-[3,4 gh]-[1,4]benzoxazine, m.p. turns brown 200° melt 210°-213°.

Workup

  1. customThe catalyst is removed by filtration
  2. customthe solvent is removed under reduced pressure (20 mm)
  3. customThe oil is recrystallized from methanol

Sources & evidence

ORD record
ord-06e7e7f5280f4cf08c69511a09a0f74a
Source dataset
uspto-grants-1980_12
Patent number
US04238486

Reaction notes

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