4-Nitroaniline → HCID 135962047, compound

HRID 1654372Notes

Reaction equation

HRID 1654372 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, Ar CH2); 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.13/25 H2O: 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-ce9a26631a1e4ef4902347c19218b4bc
Source dataset
uspto-grants-1995_04
Patent number
US05405851

Reaction notes

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