Sodium Carbonate → HCID 135618014, compound

HRID 2165904Notes

Reaction equation

HRID 2165904 reaction equation
[N:1]1[O:2][C:3]2[CH2:4][CH2:5][CH2:6][C:7]3[C:16]=2[C:15]=1[C:14]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:8]=3.C([BH3-])#N.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[N:1]1[O:2][C:3]2[CH2:4][CH2:5][CH2:6][CH:7]3[C:16]=2[C:15]=1[C:14]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:8]3

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 5325766HCID 5325766, compound

Product 1

HCID 135618014HCID 135618014, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 100 ml glacial acetic acid was dissolved 4.75 g 4,5-dihydro-3H-isoxazolo[5,4,3-kl]acridine. To the mechanically stirred solution under nitrogen was added 2.84 g of sodium cyanoborohydride. The reaction was complete after 0.5 hour at room temperature. The reaction mixture was neutralized with excess aqueous sodium carbonate and extracted with dichloromethane (DCM). The DCM was dried over MgSO4, filtered and concentrated to a solid. The solid was purified by flash chromatography and recrystallized from 1:1 DCM/hexanes to yield 2.78 g of powder, m.p. 152°-154° C.

Workup

  1. extractionextracted with dichloromethane (DCM)
  2. dry with materialThe DCM was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to a solid
  5. customThe solid was purified by flash chromatography
  6. customrecrystallized from 1:1 DCM/hexanes

Sources & evidence

ORD record
ord-471facdd4e7d4ef2a5fd5d59cfa31a7f
Source dataset
uspto-grants-1990_07
Patent number
US04942237

Reaction notes

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