5-Chloro-2-nitroaniline → 5-(2-Methoxymethyl-pyrrol-1-yl)-2-nitro-phenylamine

HRID 1266742Notes

Reaction equation

HRID 1266742 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.CO[C:28]1([CH2:35]OC)[CH2:32][CH2:31][CH:30]([O:33][CH3:34])O1>CC(O)=O>[CH3:34][O:33][CH2:30][C:31]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:35]=[CH:28][CH:32]=1

Participants

5

Reactant 3

HCID 742185-Chloro-2-nitroanilineHCID 18548776N-(5-amino-2-nitro-phenyl)-acetamideHCID 185488962,5-Dimethoxy-2-methoxymethyl-tetrahydro-furan

Product 1

HCID 185488175-(2-Methoxymethyl-pyrrol-1-yl)-2-nitro-phenylamine

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-2-methoxymethyl-tetrahydro-furan [CAS-no. 98560-90-8] in HOAc at 60° C. for 2 h according to the general procedure F. Obtained as a light brown solid (620 mg). Deacetylation of this material was perfomed by stirring with 2 eq. 2 N NaOH-sol. in 1,4-dioxane at 60° C. for 21 h. Obtained as a yellow solid (511 mg).

Workup

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

Sources & evidence

ORD record
ord-3b5f60c50e3741d7b669879ebb68e46a
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

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