HCID 68136758, compound → HCID 68137053, compound

HRID 1731093Notes

Reaction equation

HRID 1731093 reaction equation
[CH2:1]([O:8][C:9]1[CH:29]=[CH:28][C:12]([CH:13]([OH:27])[CH2:14][N:15]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:11][C:10]=1[N+:30]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Fe].C(O)(=O)C>[NH2:30][C:10]1[CH:11]=[C:12]([CH:28]=[CH:29][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:13]([OH:27])[CH2:14][N:15]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:16]([CH3:18])([CH3:19])[CH3:17]

Participants

4

Reactant 1

HCID 68136758HCID 68136758, compound

Product 1

HCID 68137053HCID 68137053, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

In 150 ml. of a 50% aqueous acetic acid solution there was dissolved 30 g. of 4-benzyloxy-3-nitro-α-(N-benzyl-N-tert-butylaminomethyl) benzyl alcohol and after adding to the solution 12 g. of iron powder, the mixture was refluxed for 25 minutes, accompanied by heating. While the reaction mixture was still hot, it was filtered and the filtrate was concentrated under a reduced pressure. Then, after adding to the residue 50 ml. of a 10% aqueous sodium carbonate solution, the product was extracted with benzene. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a crystalline residue. By recrystallizing the product from a mixture of 40 ml. of benzene and 60 ml. of n-hexane, 23 g. of 3-amino-4-benzyloxy-α-(N-benzyl-N-tert-butylaminomethyl) benzyl alcohol melting at 68°-69° C was obtained.

Workup

  1. temperatureby heating
  2. filtrationit was filtered
  3. concentrationthe filtrate was concentrated under a reduced pressure
  4. additionThen, after adding to the residue 50 ml
  5. extractionof a 10% aqueous sodium carbonate solution, the product was extracted with benzene
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto give a crystalline residue
  10. customBy recrystallizing the product
  11. additionfrom a mixture of 40 ml

Sources & evidence

ORD record
ord-bcfda9ec04b4453097755c2b03e75910
Source dataset
uspto-grants-1976_11
Patent number
US03994974

Reaction notes

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