HCID 18183116, compound → HCID 18183117, compound

HRID 430662Notes

Reaction equation

HRID 430662 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH2:10][C:9]3[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:8]=3[C:7]([C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=3)=[N:6][N:5]2[C:26]=1[CH3:27]>C(O)(=O)C.[Fe]>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([C:7]2[C:8]3[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:9]=3[CH2:10][C:4]3=[N:3][C:2]([CH3:1])=[C:26]([CH3:27])[N:5]3[N:6]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 1

HCID 18183116HCID 18183116, compound

Product 1

HCID 18183117HCID 18183117, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Procedure

834 mg of 2,3-dimethyl-8-methoxy-6-(4-nitrophenyl)-11H-imidazo[1,2-c][2,3]benzodiazepine in 33 ml of glacial acetic acid together with 2.25 g of iron powder are heated for 20 minutes in an oil bath that is preheated to 90° C. It is suctioned off hot and rewashed with glacial acetic acid. The filtrate is concentrated by evaporation, and the residue is dispersed in ethyl acetate and 1N sodium hydroxide solution. The aqueous phase is shaken out twice with ethyl acetate, and the collected organic phase is washed with water, dried, filtered and concentrated by evaporation. This residue is chromatographed on silica gel with methylene chloride:ethanol=10:1 as an eluant. After the corresponding fractions that are concentrated by evaporation are absorptively precipitated with ethyl acetate/hexane, 331 mg of 6-(4-aminophenyl)-2,3-dimethyl-8-methoxy-11H-imidazo[1,2-c][2,3]benzodiazepine with a melting point of 280° C. is obtained.

Workup

  1. customis preheated to 90° C
  2. concentrationThe filtrate is concentrated by evaporation
  3. additionthe residue is dispersed in ethyl acetate
  4. washthe collected organic phase is washed with water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation
  8. customThis residue is chromatographed on silica gel with methylene chloride
  9. concentrationAfter the corresponding fractions that are concentrated by evaporation
  10. customare absorptively precipitated with ethyl acetate/hexane, 331 mg of 6-(4-aminophenyl)-2,3-dimethyl-8-methoxy-11H-imidazo[1,2-c][2,3]benzodiazepine with a melting point of 280° C.
  11. customis obtained

Sources & evidence

ORD record
ord-ace3be2877d94b14959eb38e6e2ef402
Source dataset
uspto-grants-2001_11
Patent number
US06323197B1

Reaction notes

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