Sodium Hydroxide → HCID 67325692, compound

HRID 520822Notes

Reaction equation

HRID 520822 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[C:17]([CH:18]=1)=[N:16][C:15]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=1[C:9]=2[CH3:19])=[O:4].[OH-].[Na+]>C1COCC1.O>[CH3:19][C:9]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:15]=2[N:16]=[C:17]2[C:8]=1[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:18]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67325206HCID 67325206, compound

Product 1

HCID 67325692HCID 67325692, compoundYield 259%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution 9-methyl-5,6,7,8-tetrahydro-acridine-3-carboxylic acid methyl ester (120 mg, 0.04mmols) in THF:water (6 mL:4 mL) added solid sodium hydroxide (75 mg, 0.16mmols) and heated the reaction mixture at 70° C. for 3 h. Reaction completion was monitored by TLC. Alter completion, the reaction mixture was diluted with water and washed with ethyl acetate. The aqueous layer was acidified to pH 3-4 using 1.5N hydrochloric acid solution. Precipitated product was filtered and dried to get the pure product as off white solid (25 mg, 22%). Compound was purified by preparative HPLC.

Workup

  1. customReaction completion
  2. washwashed with ethyl acetate
  3. filtrationPrecipitated product was filtered
  4. customdried

Sources & evidence

ORD record
ord-1f4eb8c081bf4dc4afee4ad390f46c74
Source dataset
uspto-grants-2016_05
Patent number
US09328093B2

Reaction notes

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