HCID 10737142, compound → HCID 10735084, compound

HRID 366830Notes

Reaction equation

HRID 366830 reaction equation
[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]([N+:16]([O-])=O)=[CH:7][C:6]=2[N:5]([C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[CH2:4]1>C1C=CC=CC=1.O=[Pt]=O>[NH2:16][C:8]1[C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[C:11]2[CH:3]([CH2:2][Cl:1])[CH2:4][N:5]([C:19](=[O:24])[C:20]([F:21])([F:22])[F:23])[C:6]=2[CH:7]=1

Participants

4

Reactant 1

HCID 10737142HCID 10737142, compound

Product 1

HCID 10735084HCID 10735084, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 241BenzeneSolvent

Procedure

A solution of the above nitro compound (175 mg, 0.49 mmol) in benzene (30 mL) was hydrogenated over PtO2 (45 mg) at 50 psi for 1 h. Removal of the catalyst and solvent provided a solid which was recrystallised from i-Pr2O/petroleum ether to give 5-amino-1-(chloromethyl)-3-trifluoroacetyl-1,2-dihydro-3H-benz[e]indole (143 mg, 89%), mp 177° C. 1H NMR [(CD3)2SO] δ 8.11 (d, J=8.4 Hz, 1 H, H-6), 7.80 (d, J=8.3 Hz, 1 H, H-9), 7.60 (s, 1 H, H-4), 7.50 (t, J=7.7 Hz, 1 H, H-8), 7.35 (t, J=7.7 Hz, 1 H, H-7), 6.14 (s, 2 H, NH2), 4.45 (dd, J=11.0, 8.7 Hz, 1 H, H-2), 4.33 (d, J 11.2 Hz, 1 H, H-2), 4.24-4.16 (m, 1 H, H-1), 4.03 (dd, J=11.0, 3.0 Hz, 1 H, CHHCl), 3.84 (dd, J=11.0, 7.1 Hz, 1 H, CHHCl). Anal. Calculated for C15H12ClF3N2O: C, 54.8; H, 3.7; N, 8.5; Cl, 10.8. Found: C, 55.1; H, 3.4; N, 8.6; Cl, 10.7%.

Workup

  1. customRemoval of the catalyst and solvent
  2. customprovided a solid which
  3. customwas recrystallised from i-Pr2O/petroleum ether

Sources & evidence

ORD record
ord-2b8a5ed543fb448aae63c838e10e6caf
Source dataset
uspto-grants-2000_10
Patent number
US06130237

Reaction notes

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