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p-Toluenesulfonic acid monohydrate → 1-(pyridin-4-yl)-5,7,8,9-tetrahydrocyclohepta[f]indazol-6(1H)-one

HRID 718819
Notes
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Reaction equation

HRID 718819 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[C:15]3[C:10](=[CH:11][C:12]4[CH2:24][C:19]5(OCC[O:20]5)[CH2:18][CH2:17][CH2:16][C:13]=4[CH:14]=3)[CH:9]=[N:8]2)=[CH:3][CH:2]=1.O.CC1C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[C:15]3[C:10](=[CH:11][C:12]4[CH2:24][C:19](=[O:20])[CH2:18][CH2:17][CH2:16][C:13]=4[CH:14]=3)[CH:9]=[N:8]2)=[CH:3][CH:2]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 867224271-(pyridin-4-yl)-5,7,8,9-tetrahydro-1H-spiro[cyclohepta[f]indazole-6,2'-[1,3]dioxolane]

Product 1

HCID 867224291-(pyridin-4-yl)-5,7,8,9-tetrahydrocyclohepta[f]indazol-6(1H)-oneYield 95.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

1-(Pyridin-4-yl)-5,7,8,9-tetrahydro-1H-spiro[cyclohepta[f]indazole-6,2′-[1,3]dioxolane] (31.8 g, 99 mmol) and 4-methylbenzenesulfonic acid hydrate (23.8 g, 125 mmol) were added to a round bottom flask followed by the addition of acetone (250 mL). The mixture was heated to about 60° C. for about 2 h, then about 45° C. for about 16 h. The reaction mixture was cooled to rt, filtered and the resulting solids were collected. The solids were taken into EtOAc/MeOH and neutralized with sat. aq. NaHCO3. The mixture was extracted with EtOAc (3×100 mL) and any solids that would not dissolve were collected. The organics were dried over MgSO4 and concentrated in vacuo. The collected solids and extracted material were combined to provided 1-(pyridin-4-yl)-5,7,8,9-tetrahydrocyclohepta[f]indazol-6(1H)-one (26.2 g, 95%); LC/MS, method 1, Rt=1.25 min MS m/z 278 (M+H)+, 1H NMR (400 MHz, DMSO) δ 8.73-8.68 (m, 2H), 8.43-8.41 (m, 1H), 8.03 (s, 1H), 7.95-7.90 (m, 2H), 7.73 (s, 1H), 3.19 (d, J=5.5 Hz, 2H), 3.17 (d, J=4.1 Hz, 2H), 2.54-2.48 (m, 2H), 2.00-1.87 (m, 2H).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. filtrationfiltered
  3. customthe resulting solids were collected
  4. extractionThe mixture was extracted with EtOAc (3×100 mL)
  5. dissolutionany solids that would not dissolve
  6. customwere collected
  7. dry with materialThe organics were dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. extractionThe collected solids and extracted material

Sources & evidence

ORD record
ord-a3c849e40e5e408cacd48d26c6c22edb
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09193744B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes