Ammonium Chloride → HCID 19871140, compound

HRID 329747Notes

Reaction equation

HRID 329747 reaction equation
[Cl-].[NH4+].[Cl:3][C:4]1[C:5]([N+:27]([O-])=O)=[C:6]([C:16]([NH:18][CH:19]2[CH:24]3[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]3)[CH2:20]2)=[O:17])[C:7]2[O:12][CH2:11][C:10](=[O:13])[N:9]([CH3:14])[C:8]=2[CH:15]=1>CN(C)C=O.[Fe]>[ClH:3].[NH2:27][C:5]1[C:4]([Cl:3])=[CH:15][C:8]2[N:9]([CH3:14])[C:10](=[O:13])[CH2:11][O:12][C:7]=2[C:6]=1[C:16]([NH:18][CH:19]1[CH:24]2[CH2:23][CH2:22][N:21]([CH2:26][CH2:25]2)[CH2:20]1)=[O:17]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 14771551HCID 14771551, compound

Product 1

HCID 19871140HCID 19871140, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 12 ml of 0.78N aqueous ammonium chloride and 5 ml of dimethylformamide with heating at 85° C. is added 4.8 g of powdery iron under stirring and then a solution of 8.0 g of 6-chloro-3,4-dihydro-4-methyl-7-nitro-3-oxo-N-(3-quinuclidinyl)-2H-1,4-benzoxazine-8-carboxamide in 40 ml of dimethylformamide is added over 10 minutes. The mixture is stirred at 80°-90° C. for an hour and filtered with suction through cellite under heating. The solvent is distilled off and to the residue is added 10 ml of cold water. The crystals are collected by filtration and washed with cold water and recrystallized from ethanol-water to give 7-amino-6-chloro-3,4-dihydro-4-methyl-3-oxo-N-(3-quinuclidinyl)-2H-1,4-benzoxazine-8-carboxamide hydrochloride, melting above 320° C. 1 -NMR(DMSO):δ(ppm)=1.40-2.30 and 2.76-4.50(each m), 3.22(s, 3H), 4.70(s,2H), 5.28(s,2H), 7.18(s,1H), 8.74(d,1H)

Workup

  1. stirringThe mixture is stirred at 80°-90° C. for an hour
  2. filtrationfiltered with suction through cellite
  3. temperatureunder heating
  4. distillationThe solvent is distilled off and to the residue
  5. additionis added 10 ml of cold water
  6. filtrationThe crystals are collected by filtration
  7. washwashed with cold water
  8. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-e2f22d40a72c43ceb9d530b57e7ae6e1
Source dataset
uspto-grants-1990_01
Patent number
US04892872

Reaction notes

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