Sodium Hydroxide → HCID 66675129, compound

HRID 2404776Notes

Reaction equation

HRID 2404776 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[NH:6]1[CH2:11][CH2:10][C:9]2([C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH2:13][CH2:12]2)[CH2:8][CH2:7]1.[OH-].[Na+].CC(OC(OC(OC(C)(C)C)=O)=O)(C)C>OS(O)(=O)=O>[N+:1]([C:17]1[CH:16]=[C:15]2[C:20]([C:9]3([CH2:10][CH2:11][NH:6][CH2:7][CH2:8]3)[CH:12]=[CH:13][NH:14]2)=[CH:19][CH:18]=1)([O-:4])=[O:2]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24434Potassium NitrateHCID 90495Di-tert-butyl dicarbonateHCID 575673872',3'-Dihydro-1'H-spiro[piperidine-4,4'-quinoline]

Product 1

HCID 66675129HCID 66675129, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

KNO3 (69.97 mg, 0.69 mmol) was added portion-wise to a suspension of 1,2,3,4-tetrahydroquinolin-4-spiro-4′-piperidine (133 mg, 0.66 mmol) in 98% H2SO4 (2 mL) at 0° C. After the addition was complete, the reaction mixture was allowed to warm to room temperature and stirred for additional 2 h. The mixture was then poured into cracked ice and basified with 10% NaOH to pH ˜8. Boc2O (172 mg, 0.79 mmol) was added dropwise and the mixture was stirred at room temperature for 1 h. The mixture was then extracted with EtOAc and the combined organic layers were dried over Na2SO4, filtered and concentrated to yield crude 7′-nitro-spiro[piperidine-4,4′(1′H)-quinoline], 2′,3′-dihydro-carboxylic acid tert-butyl ester (230 mg), which was used in the next step without further purification.

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred at room temperature for 1 h
  3. extractionThe mixture was then extracted with EtOAc
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-632cb4e490a447f8b2e32572ef9ad5f6
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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