4-(8-Methyl-9H-1,3-dioxolo(4,5-H)(2,3)benzodiazepin-5-yl)benzenamine → 1-(4-acetylaminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine

HRID 2210495Notes

Reaction equation

HRID 2210495 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](OC(=O)C)(=[O:25])[CH3:24]>C(O)C>[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:25])[CH3:24]

Participants

4

Reactant 2

HCID 35384-(8-Methyl-9H-1,3-dioxolo(4,5-H)(2,3)benzodiazepin-5-yl)benzenamineHCID 7918Acetic Anhydride

Product 1

HCID 152909021-(4-acetylaminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepineYield 76.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 g (34 mmol) of 1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine were stirred for 3 hours with 100 ml of acetic anhydride. The crystals formed were filtered, washed with 5×10 ml of anhydrous ethanol and dried, yielding 9.2 g of raw product, m.p. 252°-254° C. (decomp.). This product was treated with 45 ml of hot 99.5% ethanol. After cooling the crystals were filtered, washed with 3×10 ml of ethanol and dried to give 8.68 g (76.1%) of the aimed product, m.p.: 256°-258° C. (decomp.).

Workup

  1. customThe crystals formed
  2. filtrationwere filtered
  3. washwashed with 5×10 ml of anhydrous ethanol
  4. customdried
  5. customyielding 9.2 g of raw product, m.p. 252°-254° C. (decomp.)
  6. temperatureAfter cooling the crystals
  7. filtrationwere filtered
  8. washwashed with 3×10 ml of ethanol
  9. customdried

Sources & evidence

ORD record
ord-47c05ff80b65435fa59c46222e6c6b52
Source dataset
uspto-grants-1995_10
Patent number
US05459137

Reaction notes

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