Hydrochloric Acid → (Z)-9-(aminomethyl)-2,5-dihydrobenzo[b][1,4]dioxocine-8-carbonitrile

HRID 1186035Notes

Reaction equation

HRID 1186035 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C:13]1[C:14]([C:25]#[N:26])=[CH:15][C:16]2[O:23][CH2:22][CH:21]=[CH:20][CH2:19][O:18][C:17]=2[CH:24]=1.NN.Cl>C1COCC1>[NH2:3][CH2:12][C:13]1[C:14]([C:25]#[N:26])=[CH:15][C:16]2[O:23][CH2:22][CH:21]=[CH:20][CH2:19][O:18][C:17]=2[CH:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 58245715(Z)-9-((1,3-dioxoisoindolin-2-yl)methyl)-2,5-dihydrobenzo[b][1,4]dioxocine-8-carbonitrile

Product 1

HCID 58245722(Z)-9-(aminomethyl)-2,5-dihydrobenzo[b][1,4]dioxocine-8-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The residue prepared in STEP A above (0.34 g, 0.98 mmol) and hydrazine (0.31 ml, 9.8 mmol) were dissolved in THF (34 ml) and stirred at room temperature for 5 h. 1N HCl (22 mL) was added and the resulting mixture stirred overnight. The resulting mixture was then concentrated in vacuo and the residue was triturated with water. The water triturations were combined and concentrated in vacuo. The resulting solid was partition between ethyl acetate (50 ml) and saturated sodium bicarbonate (10 mL). The aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with brine (20 ml), dried (Na2SO4) and concentrated in vacuo to yield (Z)-9-(aminomethyl)-2,5-dihydrobenzo[b][1,4]dioxocine-8-carbonitrile as a residue.

Workup

  1. stirringthe resulting mixture stirred overnight
  2. concentrationThe resulting mixture was then concentrated in vacuo
  3. customthe residue was triturated with water
  4. concentrationconcentrated in vacuo
  5. customThe resulting solid was partition between ethyl acetate (50 ml) and saturated sodium bicarbonate (10 mL)
  6. extractionThe aqueous layer was extracted with ethyl acetate
  7. washwashed with brine (20 ml)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c5d42262fe7641528650ce271c76053e
Source dataset
uspto-grants-2014_03
Patent number
US08673890B2

Reaction notes

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