Hydrogen Bromide → HCID 12390938, compound

HRID 2419081Notes

Reaction equation

HRID 2419081 reaction equation
[BrH:1].C(OC(=O)C)(=O)C.Cl.[CH:10]1([NH:16][CH:17]2[CH2:26][CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:29]C)[C:23]=3[O:27]C)[C:18]2=[O:31])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>>[BrH:1].[CH:10]1([NH:16][CH:17]2[CH2:26][CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([OH:29])[C:23]=3[OH:27])[C:18]2=[O:31])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 7918Acetic AnhydrideHCID 12390928HCID 12390928, compound

Product 1

HCID 12390938HCID 12390938, compound

Procedure

In a mixture of 50 volume parts 48% hydrobromic acid and 15 volume parts acetic anhydride is dissolved 5 parts of 2-cyclohexylamino-5,6-dimethoxy-3,4-dihydro-1(2H)-naphthalenone hydrochloride, and the solution is heated at 140°-160° C for about 3 hours. After cooling, the solvent is removed under reduced pressure and the residue is treated with activated carbon in ethanol. Following the addition of ethyl acetate, the filtrate is allowed to stand, whereby 2-cyclohexylamino-5,6-dihydroxy-3,4-dihydro-1(2H)-naphthalenone hydrobromide is obtained as colorless prisms. Yield 4.1 parts; melting point: 225°-237° C (decomposition). Nuclear magnetic resonance spectrum

Workup

  1. temperaturethe solution is heated at 140°-160° C for about 3 hours
  2. temperatureAfter cooling
  3. customthe solvent is removed under reduced pressure
  4. additionthe residue is treated with activated carbon in ethanol
  5. additionthe addition of ethyl acetate

Sources & evidence

ORD record
ord-ae0caa857eb341b3b24476f8e71d7ce8
Source dataset
uspto-grants-1978_08
Patent number
US04104402

Reaction notes

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