3-Nitroaniline → HCID 22732303, compound

HRID 1357693Notes

Reaction equation

HRID 1357693 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].[CH3:11][N:12]([CH3:22])[C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16](Cl)=[O:17]>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[N+:1]([C:4]1[CH:5]=[C:6]([NH:7][C:16](=[O:17])[C:15]2[CH:19]=[CH:20][CH:21]=[C:13]([N:12]([CH3:11])[CH3:22])[CH:14]=2)[CH:8]=[CH:9][CH:10]=1)([O-:3])=[O:2]

Participants

6

Reactant 2

HCID 74233-NitroanilineHCID 70103423-Dimethylaminobenzoyl chloride

Product 1

HCID 22732303HCID 22732303, compoundYield 99.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

3-Nitroaniline (3.84 g) in methylene chloride (50 ml) was added dropwise to an ice-cooled solution of 3-dimethylaminobenzoyl chloride (9.74 g crude weight) and 4-dimethylaminopyridine (308 mg) in methylene chloride (30 ml) and triethylamine (8.8 ml). The reaction was stirred at ambient temperature for 72 hours and then partitioned between methylene chloride and saturated sodium bicarbonate. The organic phase was then washed with brine, dried over magnesium sulphate, filtered and evaporated to dryness affording N-(3-nitrophenyl)-3-dimethylaminobenzamide as a solid (8.64 g, 99.9%); NMR (CDCl3) 3.02 (s, 6H), 6.9 (m, 1H), 7.09 (s, 1H), 7.25 (m, 1H), 7.35 (t, 1H), 7.53 (t, 1H), 7.99 (m, 1H), 8.05 (broad s, 1H), 8.1 (m, 1H), 8.5 (m, 1H); m/s: M+H+ 286.

Workup

  1. custompartitioned between methylene chloride and saturated sodium bicarbonate
  2. washThe organic phase was then washed with brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-9be43e08bf3041d8ac7f16e3fd54beec
Source dataset
uspto-grants-2003_07
Patent number
US06593333B1

Reaction notes

Loading…