Choline, hydroxide → HCID 178492086, compound

HRID 1977224Notes

Reaction equation

HRID 1977224 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:27])[C:7]3[C:15](=[O:16])[N:14]([C:17]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=4[CH3:25])[N:13]=[C:12]([OH:26])[C:8]=3[NH:9][C:10]=2[CH:11]=1.[OH-].[OH:29][CH2:30][CH2:31][N+:32]([CH3:35])([CH3:34])[CH3:33]>CO>[OH:29][CH2:30][CH2:31][N+:32]([CH3:35])([CH3:34])[CH3:33].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:27])[C:7]3[C:15](=[O:16])[N:14]([C:17]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=4[CH3:25])[N:13]=[C:12]([OH:26])[C:8]=3[NH:9][C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 31255Choline, hydroxideHCID 178492085HCID 178492085, compound

Product 1

HCID 178492086HCID 178492086, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of 7-chloro-4-hydroxy-2-(4-methoxy-2-methylphenyl)-1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-dione (400 mg, 1.03 mM) in methanol (4 mL) was added choline hydroxide (45% by weight in methanol, 295.6 uL, 1.03 mM). After brief sonication, all solids dissolved and the resulting solution was filtered through a Gelman Glass Acrodisc filter (0.45 um) along with an additional quantity of methanol (8 mL). The filtrate was concentrated to dryness and the residual oil was stirred with isopropanol (15 mL) and ethanol (8 mL) whereupon crystallization occurred. The solids were collected and dried under vacuum at 100° C. overnight to give the title compound (411 mg, 81%) as a yellow solid, mp 229-230° C.

Workup

  1. customAfter brief sonication
  2. dissolutionall solids dissolved
  3. filtrationthe resulting solution was filtered through a Gelman Glass Acrodisc
  4. filtrationfilter (0.45 um) along with an additional quantity of methanol (8 mL)
  5. concentrationThe filtrate was concentrated to dryness
  6. customThe solids were collected
  7. customdried under vacuum at 100° C. overnight

Sources & evidence

ORD record
ord-965d3350f4e84356986f7cd2367d4a99
Source dataset
uspto-grants-2001_05
Patent number
US06232313B1

Reaction notes

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