Nitric Acid → HCID 86620258, compound

HRID 2238368Notes

Reaction equation

HRID 2238368 reaction equation
C([C:4]1[C:16]2[CH:15]=[CH:14][C:13]3[N:12]([C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH2:11][CH:10](CCl)[C:9]=3[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=O)C.[N+:25]([O-])([OH:27])=[O:26]>C(Cl)Cl>[N+:25]([C:15]1[C:16]2[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=2[C:9]2[CH2:10][CH2:11][N:12]([C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[C:13]=2[CH:14]=1)([O-:27])=[O:26]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 44549266HCID 44549266, compound

Product 1

HCID 86620258HCID 86620258, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 109 (1.0 g, 2.8 mmol) in CH2Cl2 (20 mL) was treated with fuming HNO3 (6 mL). The mixture was stirred at room temperature for 30 min, and quenched with ice. The mixture was extracted with CH2Cl2 (3×50 ml) dried, and concentrated under reduced pressure. The residue was chromatographed on silica gel, eluting with EtOAc/petroleum ether (from 1:4 to 1:1) to give 6-acetyl-1 chloromethyl)-5-nitro-3-(trifluoroacetyl)-1,2-dihydro-3H-benzo[e]indole (111) (640 mg, 57%) as a brown solid: mp 182-184° C. (EtOAc/petroleum ether); 1H NMR (CDCl3) δ 9.18 (s, 1H), 9.06 (d, J=1.4 Hz, 1H), 8.28 (dd, J=8.8, 1.6 Hz, 1H), 7.95 (d, J=8.8 Hz, 1H), 4.68-4.63 (m, 1H), 4.57-4.49 (m, 1H), 4.48-4.30 (m, 1H), 3.93-3.87 (m, 1H), 3.65-3.58 (m, 1H), 2.70 (s, 3H); 13C NMR 200.4, 154.7 (q, JC-F 39.2 Hz), 148.7, 139.2, 138.2, 130.9, 130.4, 127.7, 127.5, 125.9, 119.6, 115.7, 115.6 (q, JC-F 288H), 52.7, 45.4, 42.7, 28.5. Anal. (C17H12ClF3N2O4) C, H, N.

Workup

  1. customquenched with ice
  2. extractionThe mixture was extracted with CH2Cl2 (3×50 ml)
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed on silica gel
  6. washeluting with EtOAc/petroleum ether (from 1:4 to 1:1)

Sources & evidence

ORD record
ord-fda283becbfb46d98c72fe57f72917b0
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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