Formic Acid → 1-(4-Formylaminopheny1)-3-formyl-4-methyl-7,8-methylenedioxy-3,4-dihydro-5H-2,3-benzodiazepine

HRID 1735585Notes

Reaction equation

HRID 1735585 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:21]3[CH:22]=[C:23]4[O:28][CH2:27][O:26][C:24]4=[CH:25][C:20]=3[CH2:19][CH:18]([CH3:29])[NH:17][N:16]=2)=[CH:11][CH:10]=1.[CH:30](O)=[O:31]>>[CH:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:21]3[CH:22]=[C:23]4[O:28][CH2:27][O:26][C:24]4=[CH:25][C:20]=3[CH2:19][CH:18]([CH3:29])[N:17]([CH:30]=[O:31])[N:16]=2)=[CH:11][CH:10]=1)=[O:3]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 3539Gyki 52895HCID 7918Acetic Anhydride

Product 1

HCID 190407071-(4-Formylaminopheny1)-3-formyl-4-methyl-7,8-methylenedioxy-3,4-dihydro-5H-2,3-benzodiazepine

Conditions

Temperature
25 °C

Procedure

To 6.0 ml (0.104 mol) of acetic anhydride 3.0 ml (0.08 mol) of 100 % formic acid were added dropwise at 0° C. during 5 minutes while constant stirring. The stirring was continued at 50° C. for 15 minutes. Thereafter 1 g (3.3 mmol) of 1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-3,4-dihydro-5H-2,3benzodiazepine was added to the thus-prepared mixed anhydride. The reaction mixture was stirred at 25° C. for 1.5 hours, then poured into ice-water, the precipitate formed was filtered, washed with 4×5 ml of distilled water and dried at 80° C. to give 0.80 g of raw product. After crystallization from 3 ml of ethyl acetate 0.65 g (56.2%) of the aimed product was obtained, m.p.: 193°-195° C.

Workup

  1. customthe precipitate formed
  2. filtrationwas filtered
  3. washwashed with 4×5 ml of distilled water
  4. customdried at 80° C.

Sources & evidence

ORD record
ord-f9f49b414dad46009270618e10e10639
Source dataset
uspto-grants-1996_07
Patent number
US05536832

Reaction notes

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