N-Methylaniline → HCID 53717402, compound

HRID 863512Notes

Reaction equation

HRID 863512 reaction equation
[N+:1]([C:4]1[C:5]2[CH2:18][CH:17]([C:19](O)=[O:20])[CH2:16][C:6]=2[C:7]2[NH:8][C:9](=[O:15])[C:10](=[O:14])[NH:11][C:12]=2[CH:13]=1)([O-:3])=[O:2].C(N1C=CN=C1)(N1C=CN=C1)=O.C(N(CC)CC)C.[CH3:41][NH:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CN(C=O)C>[CH3:41][N:42]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:19]([CH:17]1[CH2:16][C:6]2[C:7]3[NH:8][C:9](=[O:15])[C:10](=[O:14])[NH:11][C:12]=3[CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]=2[CH2:18]1)=[O:20]

Participants

6

Reactant 4

HCID 7515N-MethylanilineHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 19696173HCID 19696173, compound

Product 1

HCID 53717402HCID 53717402, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 6-nitro-2,3,-dioxo-2,3,4,7,8,9-hexahydro-1H-cyclopenta[f]quinoxaline-8-carboxylic acid (1 mmol, example 78) in anhydrous DMF was treated with carbonyldiimidazole (2 mmol) and triethylamine (1 mL) and then heated at 70° C. for 45 min. After cooling to room temperature methylphenylamine (1.2 mL) was added and the mixture stirred at 50° C. for 6 h. The solvent was removed in vacuo, and the residue triturated with acetone. The solid was collected by filtration, washed with diethyl ether and dried in vacuo. Calc'd for C19H16N4O5.1.2 H2O: C, 56.77; H, 4.61; N, 13.93; found: C, 56.22; H, 4.13; N, 14.62. MS M+1 (381).

Workup

  1. additionwas added
  2. customThe solvent was removed in vacuo
  3. customthe residue triturated with acetone
  4. filtrationThe solid was collected by filtration
  5. washwashed with diethyl ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-5633eace80a440eb814cb1ce698f18e0
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

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