5-Chloro-2-nitroaniline → 5-(3-Methoxymethyl-pyrrol-1-yl)-2-nitro-phenylamine

HRID 1266741Notes

Reaction equation

HRID 1266741 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][CH:28]1[CH:32]([CH2:33]OC)[CH2:31][CH:30](OC)O1>CC(O)=O>[CH3:26][O:27][CH2:28][C:32]1[CH:31]=[CH:30][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:33]=1

Participants

5

Reactant 3

HCID 742185-Chloro-2-nitroanilineHCID 185487062,5-Dimethoxy-3-methoxymethyl-tetrahydro-furanHCID 18548776N-(5-amino-2-nitro-phenyl)-acetamide

Product 1

HCID 185488535-(3-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-3-methoxymethyl-tetrahydro-furan [prepared from (2,5-dimethoxy-tetrahydro-furan-3-yl)-methanol [CAS-no. 207119-66-2] by methylation with 2.1 eq. NaH (95%) and 5.5 eq. Mel in Et2O at 0° C. for 2 h] in HOAc at 60° C. for 18 h according to the general procedure F. Obtained as a light yellow solid (86 mg). Deacetylation of this material was perfomed by stirring with 2 eq. 2 N NaOH-sol. in 1,4-dioxane at 60° C. for 2 h. Obtained as a yellow solid (69 mg).

Workup

  1. customat 60° C.
  2. customfor 18 h

Sources & evidence

ORD record
ord-a68e62bfa17f4fc1b5181ba23c34e550
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

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