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Sodium hydride → 4-(1-amino-6-nitro-1H-indol-3-yl)-benzonitrile

HRID 2079904
Notes
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Reaction equation

HRID 2079904 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:14]=[C:13]2[C:9]([C:10]([C:15]3[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=3)=[CH:11][NH:12]2)=[CH:8][CH:7]=1)([O-:5])=[O:4].C([N:26]1C2C(=CC=C([N+]([O-])=O)C=2)C(C2C=CC(C#N)=CC=2)=C1)(C)C.S(=O)(O)[O-].[Na+]>CN(C=O)C>[NH2:26][N:12]1[C:13]2[C:9](=[CH:8][CH:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:14]=2)[C:10]([C:15]2[CH:16]=[CH:17][C:18]([C:19]#[N:20])=[CH:21][CH:22]=2)=[CH:11]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 23665763Sodium BisulfiteHCID 574421944-(1-isopropyl-6-nitro-1H-indol-3-yl)-benzonitrileHCID 574421974-(6-nitro-1H-indol-3-yl)-benzonitrile

Product 1

HCID 574422614-(1-amino-6-nitro-1H-indol-3-yl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

Add NaH (98 mg, 2.47 mmol) to 4-(6-nitro-1H-indol-3-yl)-benzonitrile (500 mg, 1.9 mmol) in DMF (10 mL) at 0° C. under N2 and stir for additional 30 min at room temperature. Add excess NH2Cl ether solution prepared according to the procedure described in J. Org. Chem. 2004, 69 (4), 1369, and stir for an hour. Add 10% sodium bisulfite and extract with EtOAc. Wash the EtOAc extracts with 10% sodium bisulfite twice and dry over MgSO4. Evaporate the solvent to give 4-(1-amino-6-nitro-1H-indol-3-yl)-benzonitrile.

Workup

  1. extractionextract with EtOAc
  2. washWash the EtOAc
  3. dry with materialdry over MgSO4
  4. customEvaporate the solvent

Sources & evidence

ORD record
ord-74d686b4718644f98a46d6d8493e6a47
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07932284B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes