Methylamine → 8-[(Methylimino)methyl]-5-(4-nitrophenyl)-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine

HRID 430650Notes

Reaction equation

HRID 430650 reaction equation
[CH:1]([C:3]1[CH2:9][C:8]2[CH:10]=[C:11]3[O:16][CH2:15][O:14][C:12]3=[CH:13][C:7]=2[C:6]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)=[N:5][N:4]=1)=O.[CH3:26][NH2:27]>ClCCl.CO.C(O)C>[CH3:26][N:27]=[CH:1][C:3]1[CH2:9][C:8]2[CH:10]=[C:11]3[O:16][CH2:15][O:14][C:12]3=[CH:13][C:7]=2[C:6]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)=[N:5][N:4]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 108930778-formyl-5-(4-nitrophenyl)-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine

Product 1

HCID 181832208-[(Methylimino)methyl]-5-(4-nitrophenyl)-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 21226129Dichloromethane methanolSolvent

Procedure

2.0 g (5.9 mmol) of 8-formyl-5-(4-nitrophenyl)-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepine is dissolved in 100 ml of a 1:1 mixture of dichloromethane-methanol-mixed with 40 ml of a 33% solution of methylamine in ethanol and allowed to stand for 24 hours at room temperature. Then, the solvent is drawn off, and the residue is boiled with 25 ml of ethanol. After filtration, 1.95 g (93%) of the title compound with a melting point of 245-247° C. (decomposition) is obtained.

Workup

  1. filtrationAfter filtration, 1.95 g (93%) of the title compound with a melting point of 245-247° C. (decomposition)
  2. customis obtained

Sources & evidence

ORD record
ord-af9ff1d1d2ff42cebe9eab2f0c4a5144
Source dataset
uspto-grants-2001_11
Patent number
US06323197B1

Reaction notes

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