Ammonium Chloride → HCID 13731005, compound

HRID 2290594Notes

Reaction equation

HRID 2290594 reaction equation
[C:1]([NH:6][C:7]1[CH:14]=[CH:13][C:12]2[O:15][CH2:16][O:17][C:11]=2[C:8]=1[CH:9]=O)(OCC)=[O:2].C([O-])(=O)C.[NH4+:22].[Cl-].[NH4+]>C(O)(=O)C.O>[CH2:16]1[O:15][C:12]2[C:11](=[C:8]3[C:7](=[CH:14][CH:13]=2)[NH:6][C:1](=[O:2])[N:22]=[CH:9]3)[O:17]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 517165Ammonium AcetateHCID 13731004HCID 13731004, compound

Product 1

HCID 13731005HCID 13731005, compoundYield 6.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

2-Carboethoxyamino-5,6-methylenedioxybenzaldehyde (5.0 g, 21.1 mmoles) was added to a suspension of ammonium acetate (1.63 g, 21.1 mmoles) and ammonium chloride (1.13 g, 21.1 mmoles) in 50 ml of acetic acid. The temperature was slowly raised to 90° C. and held there for 15 hours. The mixture was diluted with one volume of water and then extracted with ethyl acetate, after adjusting the pH to 9 with concentrated ammonium hydroxide. The ethyl acetate layers were evaporated to dryness and the residue was recrystallized first from 10% NH4OH then from methanol to give 250 mg of 5,6-methylenedioxy-2(1H)-quinazolinone (6%), mp >300° C., M+ 190. PG,10

Workup

  1. extractionextracted with ethyl acetate
  2. customThe ethyl acetate layers were evaporated to dryness
  3. customthe residue was recrystallized first from 10% NH4OH

Sources & evidence

ORD record
ord-498d38846e9a44289421529f5b6ca6d1
Source dataset
uspto-grants-1986_10
Patent number
US04617392

Reaction notes

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