Nitric Acid → Methyl 1-methyl-4-nitro-1H-pyrrole-2-carboxylate

HRID 1265487Notes

Reaction equation

HRID 1265487 reaction equation
[C:1]([O:5][C:6](NC1C=C(C(ON2C3C=CC=CC=3N=N2)=O)N(C)C=1)=[O:7])(C)(C)C.CN1C=CN=C1.[CH3:33][N:34]1[CH:38]=[CH:37][CH:36]=[CH:35]1.ClC(Cl)(Cl)C(Cl)=O.[N+:46]([O-])([OH:48])=[O:47]>>[CH3:33][N:34]1[CH:38]=[C:37]([N+:46]([O-:48])=[O:47])[CH:36]=[C:35]1[C:6]([O:5][CH3:1])=[O:7]

Participants

6

Reactant 5

HCID 944Nitric AcidHCID 13901-MethylimidazoleHCID 6420Trichloroacetyl chlorideHCID 73041-MethylpyrroleHCID 27559874-Tert-butoxycarbonylamino-1-methyl-1h-pyrrole-2-carboxylic acid benzotriazol-1yl ester

Product 1

HCID 2759930Methyl 1-methyl-4-nitro-1H-pyrrole-2-carboxylate

Procedure

Nitroesters 6 and 10 were synthesized from the inexpensive N-methylpyrrole and N-methylimidazole as outlined in Schemes 10 and 11, respectively. Each of these compounds can be prepared economically on a large scale. Methyl 1-methyl-4-nitropyrrole-2-carboxylate (6) was prepared using a modification of the reported synthesis of pyrrole-2-trichloroketone. (Bailey et al. (1971) Org. Syn. 51:101). Briefly. reaction of the inexpensive N-methylpyrrole (14) with trichloroacetylchloride followed by nitration with nitric acid gave nitropyrrole trichloroketone (15), which was treated with sodium methoxide to yield nitropyrrole (6).

Workup

  1. customEach of these compounds can be prepared economically on a large scale

Sources & evidence

ORD record
ord-103c24427ec046108c0d02c4ba87cb6f
Source dataset
uspto-grants-2003_04
Patent number
US06545162B1

Reaction notes

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