Sulfuric Acid → HCID 44549153, compound

HRID 2238412Notes

Reaction equation

HRID 2238412 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[CH:15]=[CH:14][C:13]3[N:12]([C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[CH2:11][CH:10]([CH2:22][Cl:23])[C:9]=3[C:8]=2[CH:24]=1)(=[O:3])[CH3:2].OS(O)(=O)=O.[N+:30]([O-])([O-:32])=[O:31].[K+]>>[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:15]([N+:30]([O-:32])=[O:31])=[CH:14][C:13]3[N:12]([C:16](=[O:21])[C:17]([F:19])([F:18])[F:20])[CH2:11][CH:10]([CH2:22][Cl:23])[C:9]=3[C:8]=2[CH:24]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 1118Sulfuric Acid2×HCID 24434Potassium NitrateHCID 44550855HCID 44550855, compound

Product 1

HCID 44549153HCID 44549153, compoundYield 39%

Procedure

Solid 174 (57 mg, 0.16 mmol) was dissolved in cone. H2SO4 (5 mL) at 0° C., then treated dropwise with a cold (0° C.) solution of KNO3 (16 mg, 0.16 mmol) in cone. H2SO4 (0.5 mL). After 15 min, the mixture was poured into ice water and extracted with CH2Cl2 (×6). The combined organic extracts were washed with water (×2), brine and dried. Chromatography eluting with petroleum ether/EtOAc (7:3) gave 8-acetyl-1-(chloromethyl)-5-nitro-3-(trifluoroacetyl)-1,2-dihydro-3H-benzo[e]indole (175) (25 mg, 39%) as an orange powder: mp (petroleum ether/EtOAc) 196-198° C.; 1H NMR (CDCl3) δ 9.23 (s, 1H), 8.58 (d, J=9.1 Hz, 1H, 8.49 (d, J=1.3 Hz, 1H), 8.17 (dd, J=9.1, 1.6 Hz, 1H), 4.73 (d, J=11.5 Hz, 1H), 4.56 (dd, J=11.4, 8.8 Hz, 1H), 4.47-4.39 (m, 1H), 3.98 (dd, J=11.6, 3.6 Hz, 1H), 3.77 (dd, J=11.6, 7.8 Hz, 1H), 2.78 (s, 3H). Anal. (C17H12ClF3N2O4) C, H, N.

Workup

  1. extractionextracted with CH2Cl2 (×6)
  2. washThe combined organic extracts were washed with water (×2), brine
  3. customdried
  4. washChromatography eluting with petroleum ether/EtOAc (7:3)

Sources & evidence

ORD record
ord-c62d26edf066469f8ec6af6acc3a5c5d
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

Loading…