Dimethylformamide → HCID 135624000, compound

HRID 613517Notes

Reaction equation

HRID 613517 reaction equation
CN(C)C=O.C(Cl)(=O)C(Cl)=O.[C:12]([CH2:15][C:16]1[C:25]2[C:20](=[C:21]([NH:26][C:27](=[O:36])[C:28]3[C:33]([Cl:34])=[CH:32][CH:31]=[CH:30][C:29]=3[Cl:35])[CH:22]=[CH:23][CH:24]=2)[N:19]=[CH:18][C:17]=1[CH:37]=[CH2:38])([OH:14])=O.NCC1C=CC=CN=1>ClCCl>[Cl:35][C:29]1[CH:30]=[CH:31][CH:32]=[C:33]([Cl:34])[C:28]=1[C:27]([NH:26][C:21]1[C:20]2[C:25](=[C:16]3[C:17](=[CH:18][N:19]=2)[CH:37]=[CH:38][C:12]([OH:14])=[CH:15]3)[CH:24]=[CH:23][CH:22]=1)=[O:36]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 195092-PyridinemethanamineHCID 65578Oxalyl chlorideHCID 19592572HCID 19592572, compound

Product 1

HCID 135624000HCID 135624000, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of dimethylformamide (80.5 mg) and dichloromethane (2 ml) was added oxalyl chloride (140 mg), and the mixture was stirred for 30 minutes at ambient temperature. To the mixture was added 4-carboxymethyl-8-(2,6-dichlorobenzoylamino)-3-vinylquinoline (340 mg) at 0° C., and the mixture was stirred for 30 minutes at the same temperature. To the mixture was added a solution of 2-aminomethylpyridine (458 mg) in dichloromethane (2 ml) at 0° C., and the mixture was stirred for 30 minutes at the same temperature. The mixture was partitioned between dichloromethane and saturated sodium bicarbonate solution. The organic layer was washed with saturated ammonium chloride solution and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (dichloromethane-methanol) to give 4-(2,6-dichlorobenzoylamino)-9-hydroxyphenanthridine (75.7 mg).

Workup

  1. stirringthe mixture was stirred for 30 minutes at the same temperature
  2. stirringthe mixture was stirred for 30 minutes at the same temperature
  3. customThe mixture was partitioned between dichloromethane and saturated sodium bicarbonate solution
  4. washThe organic layer was washed with saturated ammonium chloride solution and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (dichloromethane-methanol)

Sources & evidence

ORD record
ord-3c22041d60a140d0941b759da3e2f3be
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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