Hydrochloric Acid → 4-[N-Cyclopropylmethyl-(6a-methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoic acid

HRID 1097398Notes

Reaction equation

[CH:1]1([CH2:4][N:5]([C:17]2[CH:28]=[C:27]3[C:29]4[C:23]([CH3:30])([CH2:24][CH2:25][CH2:26]3)[CH2:22][CH2:21][CH2:20][C:19]=4[CH:18]=2)[C:6]2[CH:16]=[CH:15][C:9]([C:10]([O:12]CC)=[O:11])=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[OH-].[Na+].Cl>C(O)C>[CH:1]1([CH2:4][N:5]([C:17]2[CH:18]=[C:19]3[C:29]4[C:23]([CH3:30])([CH2:22][CH2:21][CH2:20]3)[CH2:24][CH2:25][CH2:26][C:27]=4[CH:28]=2)[C:6]2[CH:7]=[CH:8][C:9]([C:10]([OH:12])=[O:11])=[CH:15][CH:16]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of ethyl 4-[N-cyclopropylmethyl-(6a-methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate (0.063 g) in ethanol (5 ml) was added with 20% aqueous sodium hydroxide (1 ml), and the mixture was stirred overnight at 50° C. The reaction mixture was left to cool and then made acidic with 2 N aqueous hydrochloric acid, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was recrystallized from chloroform-n-hexane to obtain the title compound (0.042 g, yield: 71%) as colorless needles (melting point: 234-235° C.).

Workup

waitThe reaction mixture was left
temperatureto cool
extractionthe mixture was extracted with chloroform
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationThe organic layer was concentrated under reduced pressure
customthe resulting residue was recrystallized from chloroform-n-hexane

Sources & evidence

ORD record: ord-7727f0ece7d54f3b974035f06d97d108
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143260B2

Reaction notes

Loading…