Ammonium Chloride → HCID 76567880, compound

HRID 1728139Notes

Reaction equation

HRID 1728139 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:34])[C:10]3([CH:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C:13](=[O:23])[NH:12][CH:11]3[C:24]3[CH:29]=[C:28]([I:30])[CH:27]=[CH:26][C:25]=3[N+:31]([O-])=O)[C:5]2=[CH:4][CH:3]=1.[NH4+].[Cl-]>CO.[Zn]>[NH2:31][C:25]1[CH:26]=[CH:27][C:28]([I:30])=[CH:29][C:24]=1[CH:11]1[C:10]2([C:5]3[C:6](=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[NH:8][C:9]2=[O:34])[CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[CH2:14][C:13](=[O:23])[NH:12]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 76567953HCID 76567953, compound

Product 1

HCID 76567880HCID 76567880, compoundYield 61.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a suspension of racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(5-iodo-2-nitrophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione prepared in Example 201c (0.7 g, 1.15 mmol) in methanol (50 ml) was added aqueous NH4Cl solution (0.61 g, 11.5 mmol, 20 mL), followed by addition of Zn powder (0.75 g, 11.5 mmol). The reaction mixture was stirred at room temperature for 1 h, then filtered throught a short pad of celite. The filtrate was concentrated, extracted with ethyl acetate and dichloromethane. The organic layers were combined, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc, then EtOAc:MeOH=19;1) to give racemic (2′R,3R,4′S)-2′-(2-amino-5-iodophenyl)-6-chloro-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 0.41 g, 61%)

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. extractionextracted with ethyl acetate and dichloromethane
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (EtOAc

Sources & evidence

ORD record
ord-b78ccbf5f7a0454d9946b1081740a2f5
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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