Chloroacetaldehyde → HCID 66813586, compound

HRID 2176349Notes

Reaction equation

HRID 2176349 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 chromography 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 chromography on silica gel

Sources & evidence

ORD record
ord-6d647791c11548a2ac5635b2cc5d0c59
Source dataset
uspto-grants-2015_06
Patent number
US09065063B2

Reaction notes

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