Ammonium Hydroxide → 76649-95-1

HRID 1049338Notes

Reaction equation

HRID 1049338 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][C:9]([OH:11])=O.C(Cl)(=O)C(Cl)=O.[NH4+:18].[OH-]>C(Cl)Cl.CN(C=O)C.C1COCC1>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][C:9]([NH2:18])=[O:11]

Participants

7

Reactant 3

HCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 79139Norborn-2-ylacetic acid

Product 1

HCID 1181923676649-95-1Yield 97%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(bicyclo[2.2.1]heptan-2-yl)acetic acid (0.50 g, 3.24 mmol) in DCM (30 mL) was treated with oxalyl chloride (0.426 mL, 4.86 mmol), followed by a catalytic amount of DMF (1 drop) and stirred at RT for 2 h. A solution of NH4OH (˜15M, 2 mL, ˜30 mmol) in THF (5 mL) was added drop wise and the mixture stirred at RT overnight. The mixture was concentrated to dryness and the residue was dissolved in EtOAc, washed with brine, dried over MgSO4 and concentrated to dryness to afford 2-(bicyclo[2.2.1]heptan-2-yl)acetamide (480 mg, 97%). 1H NMR (400 MHz, DMSO-d6): δ 7.19 (s, 1H), 6.65 (s, 1H), 2.14 (s, 1H), 1.91 (m, 3H), 1.75 (m, 1H), 1.35 (m, 4H), 1.11 (m, 4H); MS (ESI) m/z: 154.2 (M+H+).

Workup

  1. stirringthe mixture stirred at RT overnight
  2. concentrationThe mixture was concentrated to dryness
  3. dissolutionthe residue was dissolved in EtOAc
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9bedf5c9e5d1435ead71d17ad91174b0
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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