Boron trifluoride etherate → HCID 86740707, compound

HRID 1380085Notes

Reaction equation

HRID 1380085 reaction equation
[CH:1](=[C:8]1[C:12]2=[N:13][C:14]3[CH:15]=[C:16]([NH:22][C:23](/[CH:25]=[CH:26]\[C:27]([OH:29])=[O:28])=[O:24])[CH:17]=[CH:18][C:19]=3[C:20](=[O:21])[N:11]2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(F)(F)F.[CH3:34]COCC>CO>[CH:1](=[C:8]1[C:12]2=[N:13][C:14]3[CH:15]=[C:16]([NH:22][C:23](/[CH:25]=[CH:26]\[C:27]([O:29][CH3:34])=[O:28])=[O:24])[CH:17]=[CH:18][C:19]=3[C:20](=[O:21])[N:11]2[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 70456381HCID 70456381, compound

Product 1

HCID 86740707HCID 86740707, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(Z)-3-[N-(3-benzylidene-9-oxo-1,2,3,9-tetrahydro-pyrrolo[2,1-b]quinazolin-6-yl)-aminocarbonyl]-2-propenoic acid (1.22 g) was heated in anhydrous methanol (190 ml) containing boron trifluoride etherate (1.58 ml) at reflux temperature for 8 hours. The reaction mixture was concentrated to a small volume in vacuo and the precipitate was filtered and washed with water until neutral to give 1.1 g of (Z)-3-[N-(3-benzylidene-9-oxo-1,2,3,9-tetrahydro-pyrrolo[2,1-b]quinazolin-6-yl)-aminocarbonyl]-2-propenoic acid, methyl ester, m.p. 233°-235° C.

Workup

  1. temperatureat reflux temperature for 8 hours
  2. concentrationThe reaction mixture was concentrated to a small volume in vacuo
  3. filtrationthe precipitate was filtered
  4. washwashed with water until neutral

Sources & evidence

ORD record
ord-36ffcb54763e4f28a393d6b1183d2cbd
Source dataset
uspto-grants-1986_04
Patent number
US04579847

Reaction notes

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