Chloroacetaldehyde → HCID 66813586, compound

HRID 924554Notes

Reaction equation

HRID 924554 reaction equation
[Br:1][C:2]1[C:15]2[C:6](=[C:7]3[C:12](=[C:13]([NH2:16])[N:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8]3)[CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].Cl[CH2:23][CH:24]=O>CC(O)C>[Br:1][C:2]1[C:15]2[N:14]3[CH:23]=[CH:24][N:16]=[C:13]3[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 516892Sodium BicarbonateHCID 57437655HCID 57437655, compound

Product 1

HCID 66813586HCID 66813586, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of 4-bromo-6-aminophenanthridine (19.11 g, 69.91 mmole), sodium bicarbonate (12.3 g, 146 mmole) in 2-propanol (200 ml) was added chloroacetaldehyde (50% aqueous soln. 17.35 g). After the reaction mixture was heated at 75° C. for 5 hrs., the solvent was removed. The residue was redissolved in methylene chloride and washed with water. The organic fractions were combined, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude mixture was purified by chromatography on silica gel using hexane/ethyl acetate (80/20) to obtain the title compound (13 g, 62%).

Workup

  1. custom, the solvent was removed
  2. dissolutionThe residue was redissolved in methylene chloride
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude mixture was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-32504635c7ca44399b981e3d7d117331
Source dataset
uspto-grants-2016_03
Patent number
US09281483B2

Reaction notes

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