Hydrochloric Acid → 1-(4-Dimethylamino-naphthalene-1-carbonyl)-6,7-dimethoxy-isoquinoline-4-carboxylic acid

HRID 1822764Notes

Reaction equation

HRID 1822764 reaction equation
[CH3:1][N:2]([CH3:31])[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=3)[C:18]([C:29]#N)=[CH:17][N:16]=2)=[O:14])=[CH:5][CH:4]=1.[OH-:32].[Na+].Cl.C[OH:36]>>[CH3:1][N:2]([CH3:31])[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=3)[C:18]([C:29]([OH:36])=[O:32])=[CH:17][N:16]=2)=[O:14])=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 221701831-(4-Dimethylamino-naphthalene-1-carbonyl)-6,7-dimethoxy-isoquinoline-4-carbonitrile

Product 1

HCID 114303361-(4-Dimethylamino-naphthalene-1-carbonyl)-6,7-dimethoxy-isoquinoline-4-carboxylic acid

Conditions

Temperature
90 °C

Procedure

To the suspension of 1-(4-dimethylamino-naphthalene-1-carbonyl)-6,7-dimethoxy-isoquinoline-4-carbonitrile (31 mg, 0.082 mmol) in methanol (2 mL) was added 25% of aqueous sodium hydroxide solution (0.27 mL, 1.68 mmol). The mixture was stirred at 90° C. for 12 h. After cooling to room temperature, the reaction was adjusted to pH=2 with 2 N HCl solution. The product was extracted with chloroform (2×200 mL). The combined organic layers were washed with water (3×50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified directly by HPLC (Reverse C18, 10%–90% acetonitrile in water in 10 min) afforded our desired product 1-(4-dimethylamino-naphthalene-1-carbonyl)-6,7-dimethoxy-isoquinoline-4-carboxylic acid (9 mg) as a solid. LC/MS m/e calcd for C25H22N2O5 (MH+) 431. found 431.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe product was extracted with chloroform (2×200 mL)
  3. washThe combined organic layers were washed with water (3×50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified directly by HPLC (Reverse C18, 10%–90% acetonitrile in water in 10 min)

Sources & evidence

ORD record
ord-1fcd41d7e8744e8fb6b2cb8220dd451b
Source dataset
uspto-grants-2006_05
Patent number
US07037924B2

Reaction notes

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