Hydrochloric Acid → HCID 22114771, compound

HRID 1276038Notes

Reaction equation

HRID 1276038 reaction equation
C[O:2][C:3]([C:5]1[C:6]2[C:11]([N:12]=[C:13]3[C:18]=1[CH:17]=[CH:16][C:15]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=1)=[CH:14]3)=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:4].Cl>O1CCOCC1.[OH-].[Na+]>[N+:27]([C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[CH2:20][O:19][C:15]1[CH:16]=[CH:17][C:18]2[C:13]([CH:14]=1)=[N:12][C:11]1[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:5]=2[C:3]([OH:4])=[O:2])([O-:29])=[O:28]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54230499HCID 54230499, compound

Product 1

HCID 22114771HCID 22114771, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

3-(m-Nitrobenzyloxy)acridine-9-carboxylic acid methylester (6.5 g; 16.7 mmol) was refluxed in 400 ml dioxane and 300 ml NaOH 1N. After 2 hours the solution was cooled and acidified to pH 1 with HCl conc., then evaporated in vacuo. The precipitate was collected on a Buchner funnel, washed with water and dried in vacuo at 50° C. Yield 5.9 g (95%), Fp.>250° C. 1H-NMR(DMSO-d6): 8.44(1H, s, ar.); 8.23(1H, d, ar.); 8.10(2H, t, ar.); 8.03(1H, d, ar.); 7.95(1H, d, ar.); 7.72(2H. m, ar.); 7.42(2H, m, ar.); 7.27(1H, d, ar.); and 5.50 ppm (2H, s, CH2). MS: M+ =374.

Workup

  1. temperatureAfter 2 hours the solution was cooled
  2. customevaporated in vacuo
  3. customThe precipitate was collected on a Buchner funnel
  4. washwashed with water
  5. customdried in vacuo at 50° C
  6. custom>250° C

Sources & evidence

ORD record
ord-9237e7a14cf64c46a3ce8a32541f4b0d
Source dataset
uspto-grants-2000_12
Patent number
US06165800

Reaction notes

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