Ethanol → HCID 21324990, compound

HRID 26189

Reaction equation

HRID 26189 reaction equation
[CH2:1]([OH:3])[CH3:2].[CH3:4][O:5][C:6]1[C:7]([N+:17]([O-:19])=[O:18])=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH2:11][CH2:10][CH2:9]2.Cl.[NH:21]1[CH2:26]CO[CH2:23][CH2:22]1.C(=O)([O-])O.[Na+]>O.C(OCC)C>[CH3:4][O:5][C:6]1[C:7]([N+:17]([O-:19])=[O:18])=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH:11]([CH2:26][N:21]1[CH2:22][CH2:23][O:3][CH2:1][CH2:2]1)[CH2:10][CH2:9]2

Participants

7

Reactant 4

HCID 702EthanolHCID 197884Morpholine, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 130673376-Methoxy-5-nitro-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 21324990HCID 21324990, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

In 100 ml. of ethanol is dissolved a mixture of 1 g. of 6-methoxy-5-nitro-3,4-dihydro-1(2H)-naphthalenone and 3 g. of morpholine hydrochloride and the mixed solution is reacted at 80° C. for 10 hours. The reaction mixture is cooled and, following addition of 500 ml. of water, it is shaken with 100 ml. of diethyl ether. The water layer is neutralized with sodium hydrogen carbonate and extracted with chloroform. The extract is dried and distilled under reduced pressure to remove the solvent. By the above procedure is obtained 6-methoxy-2-morpholinomethyl-5-nitro-3,4-dihydro-1(2H)-naphthalenone as an oily product. This product is dissolved in 50 ml. of methanol and, after addition of 1 g. of sodium borohydride, the solution is stirred at room temperature for 30 minutes. To this reaction mixture is added 500 ml. of water and the mixture is extracted with chloroform. The extract is dried and distilled under reduced pressure to remove the solvent. The above procedure provides an oil of 6-methoxy-2-morpholinomethyl-5-nitro-1,2,3,4-tetrahydro-1-naphthalenol. This product is dissolved in 20 ml. of ethanolic hydrochloric acid and the solution is heated at 80° C. for 1 hour. Following the addition of 50 ml. of ethyl acetate, the solution is cooled, whereupon 0.35 g. of 7-methoxy-3-morpholinomethyl-8-nitro-1,2-dihydronaphthalene hydrochloride is obtained as pale-yellow prisms melting at 200°-270° C. (gradually decomposed).

Workup

  1. additiona mixture of 1 g
  2. temperatureThe reaction mixture is cooled
  3. additionaddition of 500 ml
  4. extractionextracted with chloroform
  5. customThe extract is dried
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent

Sources & evidence

ORD record
ord-eebd0246bce042a592c82726ed11085e
Source dataset
uspto-grants-1979_04
Patent number
US04148897

Linked notes

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