Hydrazine → (2,3-Dihydrobenzofuran-2-yl)methanamine

HRID 216252Notes

Reaction equation

HRID 216252 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH:2]1[CH2:10][N:11]1C(=O)C2C(=CC=CC=2)C1=O.NN>CO.C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH:2]1[CH2:10][NH2:11]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 690694492-(2,3-Dihydro-benzofuran-2-ylmethyl)-isoindole-1,3-dione

Product 1

HCID 29905(2,3-Dihydrobenzofuran-2-yl)methanamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2,3-dihydro-benzofuran-2-ylmethyl)-isoindole-1,3-dione (0.97 g, 3.47 mmol) in MeOH (15 mL) and CH2Cl2 (5 mL) is added hydrazine (0.55 mL, 17.4 mmol). After 20 h at rt, the mixture is filtered off and the filtrate is concentrated. The residue is diluted with water (50 mL), and extracted with CH2Cl2 (2×50 mL). The extracts are dried (MgSO4), filtered, and concentrated to afford C-(2,3-dihydro-benzofuran-2-yl)-methylamine, which is used for a next step without further purification. LCMS: RT=1.25 minutes; MS: 150 (M+H).

Workup

  1. filtrationthe mixture is filtered off
  2. concentrationthe filtrate is concentrated
  3. additionThe residue is diluted with water (50 mL)
  4. extractionextracted with CH2Cl2 (2×50 mL)
  5. dry with materialThe extracts are dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8bb2390c7896474aa51aa7d3816badb9
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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