5-Chloro-2-nitroaniline → 1-(3-Amino-4-nitro-phenyl)-1H-pyrrole-2-carboxylic acid methyl ester

HRID 1266743Notes

Reaction equation

HRID 1266743 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([NH:8]C(=O)C)[CH:7]=1.ClC1C=CC([N+]([O-])=O)=C(C=1)N.[CH3:26][O:27][C:28]([C:30]1(OC)[CH2:34][CH2:33][CH:32](OC)O1)=[O:29]>CC(O)=O>[CH3:26][O:27][C:28]([C:30]1[N:1]([C:2]2[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([NH2:8])[CH:7]=2)[CH:32]=[CH:33][CH:34]=1)=[O:29]

Participants

5

Reactant 3

HCID 742185-Chloro-2-nitroanilineHCID 13152840Methyl 2,5-dimethoxyoxolane-2-carboxylateHCID 18548776N-(5-amino-2-nitro-phenyl)-acetamide

Product 1

HCID 697798571-(3-Amino-4-nitro-phenyl)-1H-pyrrole-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The title compound was prepared from N-(5-amino-2-nitro-phenyl)-acetamide [prepared from commercially available 5-chloro-2-nitroaniline as described in Example F6] and 2,5-dimethoxy-tetrahydro-furan-2-carboxylic acid methyl ester [CAS-no. 39658-49-6] in HOAc at 60° C. for 2 h according to the general procedure F. Obtained as a light yellow solid (757 mg). Deacetylation of this material was perfomed by stirring with 10 eq. NaOMe-sol. in MeOH at 23° C. for 1 h. Obtained as a yellow solid (594 mg).

Workup

  1. customat 60° C.
  2. customfor 2 h

Sources & evidence

ORD record
ord-93c42405e2b54655a13fc303273462ef
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

Loading…