Dimethylformamide → HCID 67858849, compound

HRID 1587411Notes

Reaction equation

HRID 1587411 reaction equation
N[C:2]1[CH:25]=[CH:24][C:5]([NH:6][C:7]2[C:16]3[NH:15][C:14]4=[C:17]5[C:22](=[CH:23][C:13]4=[CH:12][C:11]=3[CH:10]=[CH:9][CH:8]=2)[CH:21]=[CH:20][CH:19]=[CH:18]5)=[C:4]([O:26][CH3:27])[CH:3]=1.[C:28]([O-:31])([O-])=[O:29].[K+].[K+].Br[CH2:35]C(OC)=O.[CH3:40][N:41](C=O)C>>[CH3:35][C:2]1[CH:25]=[CH:24][C:5]([N:6]([NH:41][CH2:40][C:28]([OH:31])=[O:29])[C:7]2[C:16]3[NH:15][C:14]4=[C:17]5[C:22](=[CH:23][C:13]4=[CH:12][C:11]=3[CH:10]=[CH:9][CH:8]=2)[CH:21]=[CH:20][CH:19]=[CH:18]5)=[C:4]([O:26][CH3:27])[CH:3]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 21641277HCID 21641277, compound

Product 1

HCID 67858849HCID 67858849, compound

Procedure

6-(4-Amino-2-methoxyanilino)-indeno[3,2-b]quinoline (500 mg, 1.4 mmol) synthesized in Example 4 was dissloved in 5 ml of dried DMF and 500 mg (3.5 mmol) of K2CO3 was added to this solution. To this mixing solution, BrCH2COOCH3 0.16 ml (1 5mmol) was added and heated at 50° to 60° C. for 2 hours. After heating, the reaction mixture was poured into ice water and subjected to extraction with ethyl acetate. The extract solution was dried with MgSO4 and the solvent was distilled off to obtain quantitatively 6-(4-methylcarboxymethylamino-2-methoxyanilino)-indeno[3,2-b]quinoline.

Workup

  1. temperatureheated at 50° to 60° C. for 2 hours
  2. temperatureAfter heating
  3. extractionsubjected to extraction with ethyl acetate
  4. dry with materialThe extract solution was dried with MgSO4
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-d634ac2f97b24affa01b82da5ddcaa6a
Source dataset
uspto-grants-1993_06
Patent number
US05217961

Reaction notes

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