Ammonium Chloride → 6-amino-2,3-dihydro-1H-inden-1-one

HRID 1725905Notes

Reaction equation

HRID 1725905 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][C:10]2=[O:13])=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+]>C(O)C.[Cl-].[Na+].O.[Fe]>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][C:10]2=[O:13])=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 905626-Nitroindan-1-one

Product 1

HCID 3128956-amino-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

A solution of Example 129A (19.68 g, 111 mmol) in ethanol (111 mL) was treated sequentially with iron powder (43.0 g, 770 mmol) and solid ammonium chloride (3.70 g, 69.2 mmol). The resulting suspension was stirred at 90° C. for 1 hour, cooled to room temperature, diluted with brine, and extracted with diethyl ether (4×100 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated to provide the desired product as a 6:1 mixture of 6-amino- and 4-amino-1-indanone (14.20 g, 87%). 1H NMR (300 MHz, DMSO-d6, 6-amino-1-indanone) δ 7.21 (d, 1H), 6.92 (dd, 1H), 6.75 (d, 1H), 5.27 (br s, 2H), 2.90 (t, 2H), 2.54 (m, 2H); 1H NMR (300 MHz, DMSO-d6), 4-amino-1-indanone) δ 7.10 (t, 1H), 6.81 (m, 2H), 2.80 (m, 2H), 2.59 (m, 2H).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with diethyl ether (4×100 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c8ecc4362a8049c2b0d2064bcd93cbaf
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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