Trifluoroacetic acid → [2-(3,4-Dihydro-1H-isoquinolin-2-yl)ethyl]-(7-nitro-3,4-dihydro-2H-naphthalen-1-ylidene)amine

HRID 914991Notes

Reaction equation

HRID 914991 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH2:11][CH2:12][NH2:13].[N+:14]([C:17]1[CH:26]=[C:25]2[C:20]([CH2:21][CH2:22][CH2:23][C:24]2=O)=[CH:19][CH:18]=1)([O-:16])=[O:15].C(O)(C(F)(F)F)=O>C1(C)C=CC=CC=1.CCOC(C)=O>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH2:11][CH2:12][N:13]=[C:24]1[C:25]2[C:20](=[CH:19][CH:18]=[C:17]([N+:14]([O-:16])=[O:15])[CH:26]=2)[CH2:21][CH2:22][CH2:23]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 384457-Nitro-1-tetraloneHCID 407422-(1,2,3,4-Tetrahydroisoquinolin-2-yl)ethan-1-amine

Product 1

HCID 58958206[2-(3,4-Dihydro-1H-isoquinolin-2-yl)ethyl]-(7-nitro-3,4-dihydro-2H-naphthalen-1-ylidene)amineYield 94%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 36 (964 mg, 5.48 mmol) and 7-nitro-3,4-dihydro-2H-naphthalen-1-one (95) (1.05 g, 5.48 mmol) in toluene (30 mL) was added a catalytic amount of TFA. The reaction was heated at 130° C. overnight before it was allowed to cool to room temperature and diluted with EtOAc (100 mL). The organic solution was sequentially washed with saturated NaHCO3 (aq. 100 mL), brine (100 mL), dried over Na2SO4, and concentrated to give 96 as a brown oil (1.8 g, 94%).

Workup

  1. temperatureto cool to room temperature
  2. washThe organic solution was sequentially washed with saturated NaHCO3 (aq. 100 mL), brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-875f97cde2c04a11a6c7244706e0814f
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Reaction notes

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