Nitric Acid → HCID 44550859, compound

HRID 2238384Notes

Reaction equation

HRID 2238384 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]#[N:17])[C:9]=3[CH:8]=[CH:7][C:6]=2[N:5]([C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[CH2:4]1.[N+:24]([O-])([OH:26])=[O:25]>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]#[N:17])[C:9]=3[C:8]([N+:24]([O-:26])=[O:25])=[CH:7][C:6]=2[N:5]([C:18](=[O:23])[C:19]([F:22])([F:20])[F:21])[CH2:4]1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 44549270HCID 44549270, compound

Product 1

HCID 44550859HCID 44550859, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 126 (60 mg, 0.18 mmol) in CH2Cl2 (10 mL) was treated with fuming HNO3 (1.5 mL) and stirred for 30 min at room temperature. The reaction was quenched with ice and extracted with CH2Cl2 (3×50 ml). The extracts were 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 1-(chloromethyl)-5-nitro-3-(trifluoroacetyl)-1,2-dihydro-3H-benzo[e]indole-6-carbonitrile (127) (28 mg, 41%) as a brown solid: mp EtOAc/petroleum ether) 201-205° C. (dec.); 1H NMR [(CD3)2SO] δ 8.87 (s, 1H), 8.63 (dd, J=8.5, 1.1 Hz, 1H), 8.40 (dd, J=7.3, 1.0 Hz, 1H), 7.93 (dd, J=8.5, 7.3 Hz, 1H), 4.73-4.61 (m, 2H), 4.55-4.49 (m, 1H), 4.22-4.15 (m, 1H), 4.12-4.07 (m, 1H); 13C NMR δ 153.8 (q, JC-F 37.6 Hz), 146.8, 139.8, 137.7, 132.6, 130.3, 129.4, 128.3, 118.7, 115.4 (q, JC-F 288 Hz), 115.1, 114.8, 105.4, 52.7, 47.4, 41.1. Anal. (C16H9ClF3N3O3) C, H, N.

Workup

  1. customThe reaction was quenched 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. washeluting with EtOAc/petroleum ether (from 1:4 to 1:1)

Sources & evidence

ORD record
ord-092089acc0ee4177ba2355d4068c1b15
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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