Formaldehyde → 2,2,2-trifluoro-1-(7-nitro-3,4-dihydroisoquinolin-2(1H)-yl)ethanone

HRID 1786381Notes

Reaction equation

HRID 1786381 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)=[O:4].[CH2:19]=O.OS(O)(=O)=O>CC(O)=O>[F:1][C:2]([F:17])([F:18])[C:3]([N:5]1[CH2:6][CH2:7][C:8]2[C:13](=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[CH2:19]1)=[O:4]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 64237442,2,2-Trifluoro-N-[2-(4-nitro-phenyl)-ethyl]-acetamide

Product 1

HCID 219568152,2,2-trifluoro-1-(7-nitro-3,4-dihydroisoquinolin-2(1H)-yl)ethanone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

To the mixture of 2,2,2-trifluoro-N-[2-(4-nitro-phenyl)-ethyl]-acetamide (65 g, 0.25 mole), paraformaldehyde (42.4 g, 0.375 mole, 1.5 eq.) and HOAc (200 mL) in a 1 L round bottom flask equipped with a magnetic stirrer and a ice/water bath was added H2SO4 (300 mL) slowly while maintaining reaction temperature under 40° C. The resulting mixture was stirred for 2 h at 40° C., poured into ice, extracted with EtOAc, washed with water, sat. Na2CO3 and sat. NH4Cl, dried over Na2SO4, filtered and concentrated to give the title ethanone compound. This can be used in the next step without further purification. An analytical sample was obtained through silica gel column chromatography with eluant of CH2Cl2:MeOH (9:1).

Workup

  1. customequipped with a magnetic stirrer and a ice/water bath
  2. temperaturewhile maintaining
  3. customreaction temperature under 40° C
  4. additionpoured into ice
  5. extractionextracted with EtOAc
  6. washwashed with water, sat. Na2CO3 and sat. NH4Cl
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-bef25b9396c9487081cd1518b9b04435
Source dataset
uspto-grants-2009_03
Patent number
US07507748B2

Reaction notes

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