Hydrochloric Acid → HCID 178483245, compound

HRID 2085112Notes

Reaction equation

HRID 2085112 reaction equation
C[N:2]([CH:4]=[C:5]1[C:9]2=[C:10]3[C:15](=[CH:16][CH:17]=[C:8]2[NH:7][C:6]1=[O:18])[N:14]=[CH:13][CH:12]=[CH:11]3)[CH3:3].[CH3:19][N:20]([CH2:22][C:23]1[CH:29]=[CH:28]C(N)=[CH:25][CH:24]=1)[CH3:21].Cl>C(O)C>[CH3:19][N:20]([CH2:22][C:23]1[CH:29]=[CH:28][C:3]([NH:2]/[CH:4]=[C:5]2\[C:6](=[O:18])[NH:7][C:8]3[C:9]\2=[C:10]2[C:15](=[CH:16][CH:17]=3)[N:14]=[CH:13][CH:12]=[CH:11]2)=[CH:25][CH:24]=1)[CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 308051Benzenemethanamine, 4-amino-N,N-dimethyl-HCID 69838355HCID 69838355, compound

Product 1

HCID 178483245HCID 178483245, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of dimethylaminomethylidene-1,3-dihydro-2H-pyrrolo[3,2-f]quinoline-2-one (0.1 mmol), 4-dimethylaminomethylaniline (0.1 mmol) and conc. hydrochloric acid (0.02 mL) in ethanol (1 mL) was heated at reflux until the reaction was complete as determined by tic analysis. The reaction mixture was allowed to cool to room temperature. The solvent was evaporated and the residue purified using silica gel chromatography to give the title compound as an orange-brown solid, 15 mg. (42%). 1H NMR (DMSO-d6): δ 2.17 (s, 6H), 3.17 (s, 2H), 7.31-7.51 (m, 6H), 7.74 (d, J=8.7 Hz, 1H), 8.74 (d, J=3.3 Hz, 1H), 8.83 (d, J=6.0 Hz, 1H), 8.86 (d, J=12 Hz, 1H), 10.95 (s, 1H), 11.80 (d, J=12 Hz, 1H); APESI+MS m/z 345 (M+1)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux until the reaction
  3. customThe solvent was evaporated
  4. customthe residue purified

Sources & evidence

ORD record
ord-e9330717747a4e92a7611f4e25685d6d
Source dataset
uspto-grants-2004_04
Patent number
US06720332B2

Reaction notes

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