Sodium Hydroxide → 4,4-Dimethylchroman-7-amine

HRID 1915302Notes

Reaction equation

HRID 1915302 reaction equation
[CH3:1][C:2]1([CH3:16])[C:11]2[C:6](=[CH:7][C:8]([NH:12]C(=O)C)=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1.[OH-].[Na+]>Cl>[CH3:1][C:2]1([CH3:16])[C:11]2[C:6](=[CH:7][C:8]([NH2:12])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57470214N-(4,4-dimethyl-chroman-7-yl)-acetamide

Product 1

HCID 189835884,4-Dimethylchroman-7-amineYield 92%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of N-(4,4-dimethyl-chroman-7-yl)-acetamide (1.35 g, 6.2 mmol) in 20% HCl solution (30 mL) was heated at reflux for 3 h and then cooled to room temperature. The reaction mixture was basified with 10% aq. NaOH to pH 8 and extracted with EtOAc (30×3 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated to give 3,4-dihydro-4,4-dimethyl-2H-chromen-7-amine (C-5) (1 g, 92%). 1H NMR (DMSO-d6) δ 6.87 (d, J=8.4 Hz, 1H), 6.07 (dd, J=8.4, 2.4 Hz, 1H), 5.87 (d, J=2.4 Hz, 1H), 4.75 (s, 2H), 3.99 (t, J=5.4 Hz, 2H), 1.64 (t, J=5.1 Hz, 2H), 1.15 (s, 6H); ESI-MS 178.1 m/z (MH+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. extractionextracted with EtOAc (30×3 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-67ad61b8948a418c80024e06e8605e9d
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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