Nitric Acid → HCID 44550991, compound

HRID 2238386Notes

Reaction equation

HRID 2238386 reaction equation
[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[C:15]([C:16]([NH2:18])=[O:17])[C:9]=3[CH:8]=[CH:7][C:6]=2[N:5]([C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[CH2:4]1.[N+:25]([O-])([OH:27])=[O:26]>C(Cl)Cl>[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[C:15]([C:16]([NH2:18])=[O:17])[C:9]=3[C:8]([N+:25]([O-:27])=[O:26])=[CH:7][C:6]=2[N:5]([C:19](=[O:24])[C:20]([F:23])([F:21])[F:22])[CH2:4]1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 44549271HCID 44549271, compound

Product 1

HCID 44550991HCID 44550991, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 128 (300 mg, 0.84 mmol) in CH2Cl2 (20 mL) was treated with filming HNO3 (2 mL) for 30 min at room temperature, then quenched with ice and extracted with CH2Cl2 (3×50 ml). The extracts were dried and concentrated under reduced pressure, and the residue was chromatographed on silica gel. Elution with EtOAc/petroleum ether/methanol (from 5:1:0 to 9:0:1) gave 1-(chloromethyl)-5-nitro-3-(trifluoroacetyl)-1,2-dihydro-3H-benzo[e]indole-6-carboxamide (129) (150 mg, 45%) as yellow solid: mp 272-277° C. (EtOAc/petroleum ether); 1H NMR [(CD3)2SO] δ 8.78 (s, 1H), 8.30 (dd, J=8.4, 1.1 Hz, 1H), 8.24 (s, 1H), 7.91 (dd, J=7.1, 1.0 Hz, 1H), 7.80 (dd, J=8.4, 7.1 Hz, 11), 7.57 (s, 1H), 4.69-4.61 (m, 2H), 4.52-4.47 (m, 1H), 4.21-4.15 (m, 1H), 4.13-4.07 (m, 1H); 13C NMR δ 169.3, 153.6 (q, JC-F 37.8 Hz), 148.1, 138.6, 133.4, 132.4, 130.1, 128.7, 127.9, 126.1, 119.3, 115.6 (q, JC-F 288 Hz), 114.4, 52.7, 47.5, 41.2. Anal. (C16H11ClF3N3O4) C, H, N, Cl.

Workup

  1. customquenched with ice
  2. extractionextracted with CH2Cl2 (3×50 ml)
  3. customThe extracts were dried
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was chromatographed on silica gel
  6. washElution with EtOAc/petroleum ether/methanol (from 5:1:0 to 9:0:1)

Sources & evidence

ORD record
ord-36d8d9ca3d8b4aaf90b99c9ec6c264a9
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

Loading…