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

HRID 1841689Notes

Reaction equation

HRID 1841689 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-282c938660ab49c392d0855999642d44
Source dataset
uspto-grants-2004_01
Patent number
US06683189B1

Reaction notes

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