Water → HCID 12340629, compound

HRID 259035Notes

Reaction equation

HRID 259035 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1.[C:13]([O:18][CH2:19][CH3:20])(=[O:17])[C:14]([CH3:16])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH2:19]([O:18][C:13]([C:14]1([CH3:16])[C:9]2=[CH:10][CH:11]=[CH:12][N:8]2[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[O:1]1)=[O:17])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 12041Ethyl pyruvateHCID 7123342-(1H-Pyrrol-1-Yl)Phenol

Product 1

HCID 12340629HCID 12340629, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of the compound of formula 2, N-(2-hydroxyphenyl)pyrrole (18 g), described in Example 1, ethyl pyruvate (13 g) and p-toluenesulfonic acid (1.8 g) in benzene (1.2 1) is stirred and heated at reflux with a Dean-Stark water trap for 30 min. The reaction mixture is allowed to cool and stand at room temperature for 18 hr. The mixture is filtered and the filtrate is washed with 5% NaHCO3, water, saturated brine solution, and then dried (MgSO4). The solvent is evaporated and the remaining material is adsorbed on a silica gel column. Elution with chloroform gives 4-methyl-4H-pyrrolo[2,1-c][1,4]benzoxazine-4-carboxylic acid ethyl ester, νmaxCHCl3 1,735, 1,605, 1,510, 1,345, 1,125, 1,095 cm-1.

Workup

  1. temperatureheated
  2. temperatureto cool
  3. filtrationThe mixture is filtered
  4. washthe filtrate is washed with 5% NaHCO3, water, saturated brine solution
  5. dry with materialdried (MgSO4)
  6. customThe solvent is evaporated
  7. washElution with chloroform

Sources & evidence

ORD record
ord-117378db737640768bf03a1b9a5540dc
Source dataset
uspto-grants-1977_07
Patent number
US04035495

Reaction notes

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