Acetic Acid → 7,8-Methylenedioxy-1-(4-methylphenyl)-3,5-dihydro-2,3-benzodiazepin-4(4H)-one

HRID 442664Notes

Reaction equation

HRID 442664 reaction equation
[CH2:1]1[O:9][C:8]2[C:3](=[CH:4][C:5]([C:15](=O)[C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)=[C:6]([CH2:10][C:11](OC)=[O:12])[CH:7]=2)[O:2]1.O.[NH2:25][NH2:26].C(O)(=O)C>C(O)C>[CH2:1]1[O:2][C:3]2=[CH:4][C:5]3[C:15]([C:16]4[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=4)=[N:26][NH:25][C:11](=[O:12])[CH2:10][C:6]=3[CH:7]=[C:8]2[O:9]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 10710218Methyl 2-(4-Methylbenzoyl)-4,5-methylenedioxyphenylacetate

Product 1

HCID 106851927,8-Methylenedioxy-1-(4-methylphenyl)-3,5-dihydro-2,3-benzodiazepin-4(4H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared from methyl 4,5-methylenedioxy-2-(4-methylbenzoyl)phenylacetate (90 mg, 0.29 mmol), hydrazine hydrate (50 μL, 0.88 mmol) and acetic acid (40 μL) in ethanol (10 mL), mp: 222°-224° C. 1H NMR (CDCl3) 8.36 (s, 1H), 7.48 (d, 2H, J=8.0), 7.23 (d, 2H, J=8.0), 6.82 (s, 1H), 6.64 (s, 1H), 6.02 (s, 2H), 3.45 (s, 2H), 2.41 (s, 3H). Anal. Calcd. for C17H14N2O3 : C, 69.38; H, 4.79; N, 9.52. Found: C, 69.14; H, 4.80; N, 9.30.

Sources & evidence

ORD record
ord-f8e5f502c3da49f8b7ef411e25b66e70
Source dataset
uspto-grants-1999_04
Patent number
US05891871

Reaction notes

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