Ammonium Hydroxide → 1-{4-[(aminothio)peroxy]phenyl}-8-nitro-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide

HRID 457301Notes

Reaction equation

HRID 457301 reaction equation
[NH2:1][S:2][O:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:18]4[CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=[CH:23][C:17]=4[CH2:16][CH2:15][C:14]=3[C:13]([C:27]([O:29]CC)=O)=[N:12]2)=[CH:7][CH:6]=1.[OH-].[NH4+:33]>CO>[NH2:1][S:2][O:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:19]3[C:18]4[CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=[CH:23][C:17]=4[CH2:16][CH2:15][C:14]=3[C:13]([C:27]([NH2:33])=[O:29])=[N:12]2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 22291943ethyl 1-{4-[(aminothio)peroxy]phenyl}-8-nitro-4,5-dihydro-1H-benzo[g]indazole-3-carboxylate

Product 1

HCID 222919231-{4-[(aminothio)peroxy]phenyl}-8-nitro-4,5-dihydro-1H-benzo[g]indazole-3-carboxamideYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The material of Step 2 (718 mg, 0.0016 mol), conc. ammonium hydroxide (30 mL), and methanol (15 mL) were stirred in a stoppered flask for 72 hours. Contents were filtered to give a light amber solid (606 mg). The solid was recrystallized from acetonitrile to give the product as a light amber solid, 450 mg (68% yield). FABHRMS m/z 414.0902 (M+H, C18H16N5O5S requires 414.0872). 1H NMR (DMSO-d6/300 MHz) 8.15–7.95 (m, 3H); 7.83 (d, 2H); 7.80–7.40 (m, 6H); 3.20–2.95 (m, 4H).

Workup

  1. filtrationContents were filtered

Sources & evidence

ORD record
ord-1f6e2fac057f473f9e9392776fe2a4a0
Source dataset
uspto-grants-2007_03
Patent number
US07186743B2

Reaction notes

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