Isopropylamine → HCID 20063337, compound

HRID 1084447Notes

Reaction equation

HRID 1084447 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:11](=O)[O:10][C:9]=2[C:19]([OH:21])=[O:20])=[CH:4][CH:3]=1.[CH:22]([NH2:25])([CH3:24])[CH3:23]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:11](=[O:10])[N:25]([CH:22]([CH3:24])[CH3:23])[C:9]=2[C:19]([OH:21])=[O:20])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 106130211H-2-Benzopyran-3-carboxylic acid, 4-(4-fluorophenyl)-1-oxo-

Product 1

HCID 20063337HCID 20063337, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-(4-fluorophenyl)isocoumarin-3-carboxylic acid (59.8 g) and isopropylamine (210 ml) in ethanol (610 ml) was heated in a sealed pressure vessel at 100° C. for 16 hours. The mixture was then evaporated to dryness and the resulting residue was suspended in water (500 ml) and extracted with diethyl ether (100 ml). The layers were separated, and the aqueous layer was acidified to pH1 by treatment with concentrated hydrochloric acid. The precipitate was filtered off, washed with water, and crystallised from aqueous ethanol, to give 4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinoline-3-carboxylic acid (51.3 g) in the form of white microcrystals, m.p.128°-130° C. [Elemental analysis: C,65.0; H,5.16; N,3.98; F,5.6; H2O, 6.1%; calculated for C19H16FNO3 :1.3H2O: C,65.4; H,5.38; N,4.02; F,5.45; H2O, 6.7%].

Workup

  1. customThe mixture was then evaporated to dryness
  2. extractionextracted with diethyl ether (100 ml)
  3. customThe layers were separated
  4. filtrationThe precipitate was filtered off
  5. washwashed with water
  6. customcrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-08e28dd037d64340bc95d1fa6976b4b1
Source dataset
uspto-grants-1991_04
Patent number
US05004747

Reaction notes

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