Sulfuric Acid → HCID 23047464, compound

HRID 2107090Notes

Reaction equation

HRID 2107090 reaction equation
[C:1]1([CH:7]([N:11]([CH2:17][CH:18](OC)OC)[C:12](=O)[CH:13]([CH3:15])[CH3:14])C(O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]#[C:31][C:32]([O:34][CH3:35])=[O:33])=[CH:26][CH:25]=1.C(N(CC)CC)C.S(=O)(=O)(O)O>C(OC(=O)C)(=O)C.O>[F:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]2[C:31]([C:32]([O:34][CH3:35])=[O:33])=[C:12]([CH:13]([CH3:14])[CH3:15])[N:11]3[CH:17]=[CH:18][C:2]4[C:1](=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:7]=23)=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8471TriethylamineHCID 111268212-Propynoic acid, 3-(4-fluorophenyl)-, methyl esterHCID 23047407HCID 23047407, compound

Product 1

HCID 23047464HCID 23047464, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A suspension of 2-phenyl-2-[N-(2,2-dimethoxyethyl)-2-methylpropanamido]acetic acid (32.1 g) and methyl 4-fluorophenylpropiolate (22.5 g) in acetic anhydride (120 ml) was treated with triethylamine (16 ml) and the resulting amber solution was stirred at room temperature under argon for 24 hours. The solution was then added, dropwise during 10 minutes, to concentrated sulphuric acid (200 ml), stirring and cooling by means of an icebath. The mixture was stirred for 30 minutes and then it was poured into iced water (2.5 liters), and extracted with dichloromethane (3×400 ml). The combined extracts were washed with water (250 ml) and with brine (250 ml), dried over magnesium sulphate and evaporated, to give a brown solid, which was recrystallised from methanol, to give methyl 1-(4-fluorophenyl)-3-isopropylpyrrolo[2,1-a]isoquinoline-2-carboxylate in the form of an off-white solid, m.p. 170°-173° C.

Workup

  1. stirringstirring
  2. temperaturecooling by means of an icebath
  3. stirringThe mixture was stirred for 30 minutes
  4. extractionextracted with dichloromethane (3×400 ml)
  5. washThe combined extracts were washed with water (250 ml) and with brine (250 ml)
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customto give a brown solid, which
  9. customwas recrystallised from methanol

Sources & evidence

ORD record
ord-1b511ec5296c433782a4fc781da64fa5
Source dataset
uspto-grants-1990_06
Patent number
US04933350

Reaction notes

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