Diazomethane → HCID 70619575, compound

HRID 328699Notes

Reaction equation

HRID 328699 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([C@H:15]2[C@H:24]([OH:25])[CH2:23][C:22]3[C:21]([OH:26])=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:16]2)[CH2:11][CH2:10]1.[N+](=[CH2:29])=[N-]>CO>[CH3:29][O:26][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:22]=1[CH2:23][C@@H:24]([OH:25])[C@H:15]([N:12]1[CH2:11][CH2:10][N:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[CH2:14][CH2:13]1)[CH2:16]2

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 70619774HCID 70619774, compound

Product 1

HCID 70619575HCID 70619575, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.0 g of trans-5,6,7,8-tetrahydro-6-[4-(2-methoxyphenyl)-1-piperazinyl]-1,7-naphthalenediol in methanol is treated with about 2 equivalents of freshly prepared diazomethane. The solution is stored at 0° C for 48 hours. The solvent is removed in vacuo. The residue is dissolved in ethyl acetate, washed with dilute sodium hydroxide solution and dried. The solvent is removed in vacuo leaving an oil which crystallizes on trituration with a small amount of ether. This is washed with isopropyl ether and recrystallized from ether to give 1.7 g of the title compound, melting point 123°-125° C.

Workup

  1. customThe solvent is removed in vacuo
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. washwashed with dilute sodium hydroxide solution
  4. customdried
  5. customThe solvent is removed in vacuo
  6. customleaving an oil which
  7. customcrystallizes on trituration with a small amount of ether
  8. washThis is washed with isopropyl ether
  9. customrecrystallized from ether

Sources & evidence

ORD record
ord-17856bc8db394b03bad7c963c9603319
Source dataset
uspto-grants-1977_04
Patent number
US04018773

Reaction notes

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