HCID 19835496, compound → HCID 86743607, compound

HRID 477386Notes

Reaction equation

HRID 477386 reaction equation
[NH2:1][C:2]1[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:3]=1[O:4][CH2:5][CH:6]([OH:11])[CH2:7][N:8]([CH3:10])[CH3:9]>[Pd]>[C:3]([NH:1][C:2]1[CH:15]=[C:14]([NH:16][C:6](=[O:11])[CH3:5])[CH:13]=[CH:12][C:3]=1[O:4][CH2:5][CH:6]([OH:11])[CH2:7][N:8]([CH3:10])[CH3:9])(=[O:4])[CH3:2]

Participants

3

Reactant 1

HCID 19835496HCID 19835496, compound

Product 1

HCID 86743607HCID 86743607, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Under the conditions described in the second step of Example 10, an alcoholic solution of 0.1 mol (25.5 g) of 1-(2'-amino-4'-nitrophenoxy)-3-dimethylaminopropan-2-ol is subjected to catalytic hydrogenation in the presence of palladium-on-charcoal. The catalyst is removed by filtration, the solvent is driven off in vacuo, the oily residue is taken up in 200 ml of ethyl acetate, and 17 ml of acetic anhydride are added gradually thereto. The expected diacetylated derivative precipitates in the form of crystals. It is filtered off, washed with acetone and dried in vacuo. It melts at 118°-120° C.

Workup

  1. customThe catalyst is removed by filtration
  2. addition17 ml of acetic anhydride are added gradually
  3. customThe expected diacetylated derivative precipitates in the form of crystals
  4. filtrationIt is filtered off
  5. washwashed with acetone
  6. customdried in vacuo

Sources & evidence

ORD record
ord-d143da22dec045c88aeb2d100754061f
Source dataset
uspto-grants-1989_12
Patent number
US04888025

Reaction notes

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