Sodium Hydroxide → HCID 68842135, compound

HRID 1454821Notes

Reaction equation

HRID 1454821 reaction equation
[CH:1]1([CH2:4][O:5][CH2:6][C:7]2[N:12]=[C:11]([NH:13]C(=O)C(C)(C)C)[CH:10]=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([CH2:4][O:5][CH2:6][C:7]2[N:12]=[C:11]([NH2:13])[CH:10]=[CH:9][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68842943N-(6-Cyclopropylmethoxymethyl-pyridin-2-yl)-2,2-dimethyl-propionamide

Product 1

HCID 68842135HCID 68842135, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

N-(6-cyclopropylmethoxymethyl-pyridin-2-yl)-2,2-dimethyl-propionamide (0.884 g) in ethanol (50 mL) was treated at RT with 3M aqueous NaOH (5.62 mL) and then heated at 100° C. for 20 h. The mixture was cooled to RT, partitioned between water and AcOEt. The layers were separated, the organic layer dried over magnesium sulphate, filtered and evaporated in vacuo to give 6-cyclopropylmethoxymethyl-pyridin-2-ylamine (0.566 g) as a light brown liquid. MS (ESI): 179.1 (MH+).

Workup

  1. temperatureThe mixture was cooled to RT
  2. custompartitioned between water and AcOEt
  3. customThe layers were separated
  4. dry with materialthe organic layer dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-5fdbc0ae142344999c4e5127a0c5fd12
Source dataset
uspto-grants-2009_01
Patent number
US07482341B2

Reaction notes

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