4-Fluoroaniline → HCID 20063357, compound

HRID 1084455Notes

Reaction equation

HRID 1084455 reaction equation
[CH:1]([C:4]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:7](=[O:8])O[C:5]=1[C:15]([OH:17])=[O:16])([CH3:3])[CH3:2].[F:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1>C(OCC)C>[F:18][C:19]1[CH:25]=[CH:24][C:22]([N:23]2[C:5]([C:15]([OH:17])=[O:16])=[C:4]([CH:1]([CH3:2])[CH3:3])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:7]2=[O:8])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 20063336HCID 20063336, compound

Product 1

HCID 20063357HCID 20063357, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A suspension of 4-isopropylisocoumarin-3-carboxylic acid (24.68 g) in 4-fluoroaniline (74 ml) was refluxed under argon for 15 minutes. After cooling, the reaction mixture was dissolved in diethyl ether and the resulting solution extracted with aqueous sodium hydroxide (3×300 ml; 1M). The combined aqueous phases were washed with diethyl ether and acidified to pH1 with aqueous hydrochloric acid (2M). The resultant precipitate was filtered, washed with water and dried at 100° C. to give 2-(4-fluorophenyl)-4-isopropyl-1-oxo-1,2-dihydroisoquinoline-3-carboxylic acid (25.2 g) in the form of a white solid, m.p. 276°-277° C. (with decomposition) [Elemental analysis: C, 69.9; H, 4.9; N, 4.3%; calculated: C, 70.15; H, 4.9; N, 4.3%].

Workup

  1. temperaturewas refluxed under argon for 15 minutes
  2. temperatureAfter cooling
  3. extractionthe resulting solution extracted with aqueous sodium hydroxide (3×300 ml; 1M)
  4. washThe combined aqueous phases were washed with diethyl ether
  5. filtrationThe resultant precipitate was filtered
  6. washwashed with water
  7. customdried at 100° C.

Sources & evidence

ORD record
ord-5a1b2cdff38e4064a0320834c623d5df
Source dataset
uspto-grants-1991_04
Patent number
US05004747

Reaction notes

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