Nitric Acid → Methyl 6-nitro-1H-indole-2-carboxylate

HRID 724517Notes

Reaction equation

HRID 724517 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:10]([OH:12])=[O:11].[N+:13]([O-:16])(O)=[O:14].[C:17]1(C)C=CC(S(O)(=O)=O)=CC=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>S(=O)(=O)(O)O.C(OCC)(=O)C.C1C=CC=CC=1.CO>[CH3:17][O:11][C:10]([C:2]1[NH:1][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[C:7]([N+:13]([O-:16])=[O:14])[CH:8]=2)=[O:12]

Participants

9

Reactant 4

HCID 944Nitric AcidHCID 6101p-Toluenesulfonic acidHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 86074Indoline-2-carboxylic acid

Product 1

HCID 11816863Methyl 6-nitro-1H-indole-2-carboxylateYield 58%

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 1118Sulfuric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 34 was prepared from indoline-2-carboxlic acid by nitration with nitric acid in sulfuric acid, methylation using methanol and p-toluenesulfonic acid, followed by reaction with dichlorodicyanobenzoquinone in ethyl acetate and benzene. Total yield: 58%. MS: 219.13 (M−H+).

Sources & evidence

ORD record
ord-4e05dfd864cb491fbf2a1d1dc5317513
Source dataset
uspto-grants-2006_11
Patent number
US07141680B2

Reaction notes

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