Hydrochloric Acid → HCID 12390928, compound

HRID 596246Notes

Reaction equation

HRID 596246 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:8].[NH2:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:22][CH3:23])[C:16]=2[O:20][CH3:21])[C:11]1=[O:24].C([BH3-])#N.[Li+].O1CCOCC1.Cl>CO>[ClH:8].[CH:1]1([NH:9][CH:10]2[CH2:19][CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:22][CH3:23])[C:16]=3[O:20][CH3:21])[C:11]2=[O:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7967CyclohexanoneHCID 312751,4-DioxaneHCID 12353614HCID 12353614, compoundHCID 13171016319536-84-6

Product 1

HCID 12390928HCID 12390928, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

In a mixture of 200 volume parts of dry methanol and 200 volume parts of cyclohexanone is dissolved 10 parts of 2-amino-5,6-dimethoxy-3,4-dihydro-1(2H)-naphthalenone hydrochloride and under nitrogen sparging and cooling at 0° C, there is added 9 parts of a molecular compound consisting of 1 mole lithium cyanoborohydride and 2 moles dioxane (LiBH3CN. 2C4H8O2). At a constant temperature of 5° C, the reaction mixture is stirred for 2 hours. After the addition of dilute hydrochloric acid, the methanol is distilled off. The remaining mixture is washed with benzene and evaporated to dryness under reduced pressure. The residue is dissolved in ethanol, treated with activated carbon and recrystallized from a mixture of ethanol and ethyl ether. The procedure yields 9.65 parts of 2-cyclohexylamino-5,6-dimethoxy-3,4-dihydro-1(2H)-naphthalenone hydrochloride as colorless crystals melting at 180°-190° C (decomposition).

Workup

  1. additionthere is added 9 parts of a molecular compound
  2. distillationthe methanol is distilled off
  3. washThe remaining mixture is washed with benzene
  4. customevaporated to dryness under reduced pressure
  5. dissolutionThe residue is dissolved in ethanol
  6. additiontreated with activated carbon
  7. customrecrystallized from a mixture of ethanol and ethyl ether

Sources & evidence

ORD record
ord-628c39c9cd0741e6afdaf5d3abe72f71
Source dataset
uspto-grants-1977_03
Patent number
US04010202

Reaction notes

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