Dimethyl Sulfoxide → 3-Nitro-4-(propylamino)benzoic acid

HRID 1448086Notes

Reaction equation

HRID 1448086 reaction equation
F[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH2:14]([NH2:17])[CH2:15][CH3:16].CS(C)=O>O>[N+:11]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[NH:17][CH2:14][CH2:15][CH3:16])[C:6]([OH:8])=[O:7])([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 7852PropylamineHCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

HCID 117155563-Nitro-4-(propylamino)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 7.1 parts of 4-fluoro-3-nitrobenzoic acid, 9.1 parts of 1-propanamine and 25 parts of dimethyl sulfoxide is stirred for 3 hours at 60° C. The reaction mixture is poured onto 150 parts of water. The precipitated product is filtered off, washed with water and dried, yielding 8.8 parts of 3-nitro-4-(propylamino)benzoic acid; mp. 208° C.

Workup

  1. filtrationThe precipitated product is filtered off
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-78b0a58ae3b64669a9d98eac4a9069d6
Source dataset
uspto-grants-1979_12
Patent number
US04179505

Reaction notes

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