Pyridine → HCID 13785764, compound

HRID 1905625Notes

Reaction equation

HRID 1905625 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=2[NH:6][CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[C:8]=1[C:9]([O:11][CH3:12])=[O:10].N1C=CC=CC=1.[C:32](OC(=O)C)(=[O:34])[CH3:33]>ClCCl.CN(C)C1C=CN=CC=1>[C:32]([N:6]1[C:5]2[CH:22]=[CH:23][CH:24]=[CH:25][C:4]=2[NH:3][C:2]([CH3:1])=[C:8]([C:9]([O:11][CH3:12])=[O:10])[CH:7]1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=1)(=[O:34])[CH3:33]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 13785760HCID 13785760, compound

Product 1

HCID 13785764HCID 13785764, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2,5-dihydro-4-methyl-2-(3-nitrophenyl)-1H-1,5-benzodiazepine-3-carboxylic acid, methyl ester (800 mg., 2.36 mmole) in dichloromethane (8 ml.) is treated with pyridine (280 mg., 3.53 mmole), acetic anhydride (479 mg., 4.72 mmole) and 4-dimethylaminopyridine (5 mg.). The reaction is stirred at room temperature for 16 hours. A light yellow solid precipitates out of the reaction. The reaction is diluted with dichloromethane/methanol (100 ml. of 95:5 mixture) and the resulting solution is washed with 10% citric acid, 5% sodium bicarbonate, and brine. After drying over anhydrous magnesium sulfate, the solvent is evaporated to give a yellow foam. This foam is triturated with ether to give 705 mg. of yellow crystals. Recrystallization from dichloromethane-methanol-isopropanol gives an analytically pure sample of 1-acetyl-2,5-dihydro-4-methyl-2-(3-nitrophenyl)-1H-1,5-benzodiazepine-3-carboxylic acid, methyl ester as yellow crystals; m.p. 231°-232.5°. TLC(silica gel; acetone:hexane, 40:60) Rf = 0.28.

Workup

  1. customA light yellow solid precipitates out of the reaction
  2. additionThe reaction is diluted with dichloromethane/methanol (100 ml. of 95:5 mixture)
  3. washthe resulting solution is washed with 10% citric acid, 5% sodium bicarbonate, and brine
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. customthe solvent is evaporated
  6. customto give a yellow foam
  7. customThis foam is triturated with ether
  8. customto give 705 mg
  9. customRecrystallization from dichloromethane-methanol-isopropanol

Sources & evidence

ORD record
ord-1e702db6e6604753a64e3faa21c9ec85
Source dataset
uspto-grants-1987_03
Patent number
US04647561

Reaction notes

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