4-(8-Methyl-9H-1,3-dioxolo(4,5-H)(2,3)benzodiazepin-5-yl)benzenamine → HCID 21738598, compound

HRID 2210499Notes

Reaction equation

HRID 2210499 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]4[O:21][CH2:20][O:19][C:17]4=[CH:18][C:13]=3[CH2:12][C:11]([CH3:22])=[N:10][N:9]=2)=[CH:4][CH:3]=1.[C:23]1(=[O:30])[O:29][C:27](=[O:28])[CH2:26][CH2:25][CH2:24]1>ClCCl>[C:27]([CH2:26][CH2:25][CH2:24][C:23]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]4[O:21][CH2:20][O:19][C:17]4=[CH:18][C:13]=3[CH2:12][C:11]([CH3:22])=[N:10][N:9]=2)=[CH:4][CH:3]=1)=[O:30])([OH:29])=[O:28]

Participants

4

Reactant 2

HCID 35384-(8-Methyl-9H-1,3-dioxolo(4,5-H)(2,3)benzodiazepin-5-yl)benzenamineHCID 7940Glutaric anhydride

Product 1

HCID 21738598HCID 21738598, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.50 g (1.7 mmol) of 1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine in 30 ml of anhydrous dichloromethane was stirred with 0.18 g (1.87 mmol) of glutaric acid anhydride at 20°-25° C. for 6 hours. Next day he crystals formed were filtered at 0°-5° C., washed with 3×2 ml of dichloromethane and dried at 60°-80° C. to give 0.60 g (87.0%) or the pure aimed product, m.p. 225°-227° C. (decomp.).

Workup

  1. customNext day he crystals formed
  2. filtrationwere filtered at 0°-5° C.
  3. washwashed with 3×2 ml of dichloromethane
  4. customdried at 60°-80° C.
  5. customto give 0.60 g (87.0%)

Sources & evidence

ORD record
ord-abf079a396304dad8868b897973da544
Source dataset
uspto-grants-1995_10
Patent number
US05459137

Reaction notes

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