4-Nitroaniline → HCID 135962047, compound

HRID 1884020Notes

Reaction equation

HRID 1884020 reaction equation
[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([S:17](Cl)(=[O:19])=[O:18])[CH:15]=[CH:16][C:7]=3[CH2:6][CH2:5][C:4]=2[N:3]=1.[N+:21]([C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1)([O-:23])=[O:22]>N1C=CC=CC=1>[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:8]3[CH:13]=[C:14]([S:17]([NH:28][C:27]4[CH:29]=[CH:30][C:24]([N+:21]([O-:23])=[O:22])=[CH:25][CH:26]=4)(=[O:19])=[O:18])[CH:15]=[CH:16][C:7]=3[CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 74754-NitroanilineHCID 135622211HCID 135622211, compound

Product 1

HCID 135962047HCID 135962047, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1,2,5,6-Tetrahydro-3-methyl-1-oxobenzo[f]quinazolin-9-sulfonyl chloride (0.53 g, 1.7 mmole) and p-nitroaniline (0.25 g, 1.8 mmole) (Eastman) were dissolved in pyridine (5 ml) and the reaction mixture stirred at room temperature for 48 hours. The pyridine was removed in vacuo, and the residue washed with water. The dried solid was subjected to chromatography on silica (80 g), eluting with methanolmethylene chloride (1:19). Fractions containing product were evaporated to dryness, the residue sonicated with ether (75 ml) and filtered. The beige solid was washed with ether and dried under high vacuum to yield 1,2,5,6-tetrahydro-3-methyl-4′-nitro-1-oxobenzo[f]quinazoline-9-sulfonanilide. (0.18 g, 26%). Mp>240° C. 1H NMR (DMSO-d6, 300 MHz) δ: 2.32 (s, 3H, CH3); 2.72 (m, 2H, ArCH); 2.91 (m, 2H, ArCH2); 7.33 (d, J=9 Hz, 2H, Ar); 7.43 (d, J=8 Hz, 1H, Ar); 7.69 (dd, J=2,8 Hz, Ar); 8.13 (d, J=9 Hz, 2H, Ar); 9.23 (d, J=2 Hz, 1H, Ar); 11.13 (s, 1H, NH); 12.73 (s, 1H, NH). Anal Calculated for C19H16N4O5S.13/25H2O: C, 54.10; H, 4.07; N, 13.28; S, 7.60. Found: C, 54.07; H, 3.98; N, 13.19; S, 7.66.

Workup

  1. customThe pyridine was removed in vacuo
  2. washthe residue washed with water
  3. washeluting with methanolmethylene chloride (1:19)
  4. additionFractions containing product
  5. customwere evaporated to dryness
  6. customthe residue sonicated with ether (75 ml)
  7. filtrationfiltered
  8. washThe beige solid was washed with ether
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-aa1aa1fd100741adafcedfd675274f3b
Source dataset
uspto-grants-2004_07
Patent number
US06762188B1

Reaction notes

Loading…