Hydrochloric Acid → HCID 49757564, compound

HRID 600281Notes

Reaction equation

HRID 600281 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8]C(=O)OC(C)(C)C)=[C:4]([NH:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH3:22])[CH:3]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH3:22])[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 45379839HCID 45379839, compound

Product 1

HCID 49757564HCID 49757564, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of tert-butyl 6-chloro-4-[(2-propoxyethyl)amino]pyridin-3-ylcarbamate (7.08 g, 21.4 mmol) in 1,4-dioxane (20 mL) was treated with 4N HCl in 1,4-dioxane (100 mL) and stirred at room temperature for one hour. The reaction was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and solvent was removed at reduced pressure to give 6-chloro-N4-(2-propoxyethyl)pyridine-3,4-diamine as a brown oil. (4.93 g, 100% yield). 1H NMR (CDCl3) δ 7.63 (1H), 6.45 (1H), 4.67 (1H), 3.67 (2H), 3.43 (2H), 3.32-3.27 (2H), 2.92 (2H), 1.64-1.55 (2H), 0.93 (3H).

Workup

  1. customThe reaction was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate, and solvent
  6. customwas removed at reduced pressure

Sources & evidence

ORD record
ord-b9dee3df4bc04532822cc398e753e7be
Source dataset
uspto-grants-2011_03
Patent number
US07902195B2

Reaction notes

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