HCID 19961171, compound → HCID 19961210, compound

HRID 54136Notes

Reaction equation

HRID 54136 reaction equation
[ClH:1].C([O:5][C:6]1[C:15]([O:16]C(=O)C)=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[C:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:10]=[C:11]2[CH2:20][NH2:21])(=O)C>CO.Cl>[ClH:1].[NH2:21][CH2:20][C:11]1[C:12]2[C:7](=[C:6]([OH:5])[C:15]([OH:16])=[CH:14][CH:13]=2)[CH:8]=[C:9]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:10]=1

Participants

4

Reactant 1

HCID 19961171HCID 19961171, compound

Product 1

HCID 19961210HCID 19961210, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

5,6-Bis(acetoxy)-1-aminomethyl-3-phenylnaphthalene hydrochloride (130 mg, 0.34 mmol) from Step 3 was dissolved in 10 mL of methanol saturated with hydrogen chloride. The resultant solution was stirred at ambient temperature for 3 h and then concentrated in vacuo. The solid residue was dissolved in a minimal amount of ethanol. The ethanol solution was added slowly to 30 mL of dry diethyl ether and the precipitate was collected by filtration. The solid was dried at 60° C. in vacuo to give 77 mg (76% yield) of the title compound as a white solid, m.p. 205°-212° C. (dec); DCI MS M/Z: 266 (M+H)+, 283 (M+NH4)+ ; 1H NMR (d6 -DMSO) δ: 4.50 (d, 2H), 7.28 (d, 1H), 7.36-7.60 (m, 4H), 7.77 (s, 1H), 7.83 (d, 2H), 8.35 (s, 1H), 8.49 (br s, 3H), 9.22 (br s, 1H), 9.60 (br s, 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe solid residue was dissolved in a minimal amount of ethanol
  3. additionThe ethanol solution was added slowly to 30 mL of dry diethyl ether
  4. filtrationthe precipitate was collected by filtration
  5. customThe solid was dried at 60° C. in vacuo

Sources & evidence

ORD record
ord-c5185c52fb7d4cf28d17642557a92775
Source dataset
uspto-grants-1997_04
Patent number
US05621133

Reaction notes

Loading…