Hydrochloric Acid → HCID 68438551, compound

HRID 2242017Notes

Reaction equation

HRID 2242017 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([N+:28]([O-])=O)=[C:11]([CH2:14][CH2:15][CH2:16][N:17]2[C:21](=[O:22])[C:20]3[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=3[C:18]2=[O:27])[NH:12][CH:13]=1.Cl.O.O.Cl[Sn]Cl.[OH-].[Na+]>O1CCOCC1>[NH2:28][C:10]1[C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])=[CH:13][NH:12][C:11]=1[CH2:14][CH2:15][CH2:16][N:17]1[C:18](=[O:27])[C:19]2[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=2[C:21]1=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 68438048HCID 68438048, compound

Product 1

HCID 68438551HCID 68438551, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a round bottom flask containing a stirred solution of 2-{3-[4-(2,4-dichlorophenyl)-3-nitropyrrolyl]propyl}benzo[c]azoline-1,3-dione (4) (1 eq) and con. HCl (7 eq) in dioxane was added solid SnCl2.2H2O (10 eq) in portions. The clear yellow reaction was stirred for 12 hours at which time the reaction was found to be complete by LC/MS. The reaction was neutralized to pH 7 by addition of 6M aq. NaOH, followed by extraction with EtOAc. The organic layers were filtered and concentrated to give a solution of 2-{3-[3-amino-4-(2,4-dichlorophenyl)pyrrolyl]propyl}benzo[c]azoline-1,3-dione (5), which was unstable and used directly in the next step (LC/MS m/z 415.3 MH+). Assumed quantitative yields.

Workup

  1. customThe clear yellow reaction
  2. extractionfollowed by extraction with EtOAc
  3. filtrationThe organic layers were filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4d47250a3cb142ae89d688bf013ee406
Source dataset
uspto-grants-2010_03
Patent number
US07671049B2

Reaction notes

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