Sodium Hydroxide → 3,8-Dimethyl-1-oxo-2-phenyl-1,2-dihydro-isoquinoline-4-carboxylic acid

HRID 1920738Notes

Reaction equation

HRID 1920738 reaction equation
C([O:3][C:4]([C:6]1[C:15]2[C:10](=[C:11]([CH3:16])[CH:12]=[CH:13][CH:14]=2)[C:9](=[O:17])[N:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:7]=1[CH3:24])=[O:5])C.[OH-].[Na+]>CS(C)=O.O>[CH3:24][C:7]1[N:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9](=[O:17])[C:10]2[C:15]([C:6]=1[C:4]([OH:5])=[O:3])=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 577333143,8-Dimethyl-1-oxo-2-phenyl-1,2-dihydro-isoquinoline-4-carboxylic acid ethyl ester

Product 1

HCID 577334143,8-Dimethyl-1-oxo-2-phenyl-1,2-dihydro-isoquinoline-4-carboxylic acidYield 41.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 3,8-dimethyl-1-oxo-2-phenyl-1,2-dihydro-isoquinoline-4-carboxylic acid ethyl ester (200 mg, 0.62 mmol) in DMSO (3 ml) and aqueous 1N NaOH (2 ml, 2 mmol) was heated under microwave irradiation at +120° C. for 20 min and diluted with water (30 ml). Uncharged impurities were extracted with diethyl ether (30 ml) and the aqueous solution was poured into ice (50 g) with aqueous 2M HCl (10 ml). The obtained precipitate was filtered, washed with water and dried in vacuo to give 75 mg of yellow solid. Yield 41%. LC-MS (m/z) 293.9 (MH+); tR=1.09. 1H NMR (500 MHz, DMSO-d6): 1.95 (s, 3H), 2.74 (s, 3H), 7.3 (d, 1H), 7.32 (d, 2H), 7.48 (two overlapping m, 2H), 7.55 (t, 2H), 7.62 (t, 1H), 13.42 (b, 1H).

Workup

  1. extractionwere extracted with diethyl ether (30 ml)
  2. additionthe aqueous solution was poured into ice (50 g) with aqueous 2M HCl (10 ml)
  3. filtrationThe obtained precipitate was filtered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-549ef66e534a4790bc3c0a51b41ae6ad
Source dataset
uspto-grants-2012_05
Patent number
US08173639B2

Reaction notes

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