Sodium Hydroxide → HCID 58432798, compound

HRID 1045519Notes

Reaction equation

HRID 1045519 reaction equation
[C:1]([C:5]1[NH:6][C:7](=[O:21])[C:8]2([N:20]=1)[CH2:16][C:15]1[C:10](=[CH:11][CH:12]=[C:13]([N+:17]([O-])=O)[CH:14]=1)[CH2:9]2)([CH3:4])([CH3:3])[CH3:2].CC(C)(C)C(NC1(C(N)=O)CC2C(=CC=C([N+]([O-])=O)C=2)C1)=O.[OH-].[Na+].[NH4+].[Cl-]>CCO>[NH2:17][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C:8]1([C:7](=[O:21])[NH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[N:20]1)[CH2:16]2

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 67353772HCID 67353772, compoundHCID 67389382HCID 67389382, compound

Product 1

HCID 58432798HCID 58432798, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(±)-2-tert-Butyl-5′-nitro-1′,3′-dihydrospiro[imidazole-4,2′-inden]-5(1H)-one A solution of (±)-2-[(2,2-dimethylpropanoyl)amino]-5-nitroindane-2-carboxamide from Step A (23.0 mg, 0.075 mmol) and 5N NaOH (0.075 mL, 0.38 mmol) in EtOH (5 mL) was heated to reflux for 3.5 h. The reaction mixture was poured onto saturated NH4Cl (10 mL) and extracted with CH2Cl2 (3×10 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure to give the title compound. MS: m/z=288 (M+1).

Workup

  1. temperatureto reflux for 3.5 h
  2. extractionextracted with CH2Cl2 (3×10 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9e658ccc58f840b78b12926ceb10a516
Source dataset
uspto-grants-2013_10
Patent number
US08569291B2

Reaction notes

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