HCID 21771543, compound → HCID 11108626, compound

HRID 1476730Notes

Reaction equation

HRID 1476730 reaction equation
[I:1][C:2]1[C:3]([CH2:11][NH:12]C(=O)C)=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1>Cl>[I:1][C:2]1[C:3]([CH2:11][NH2:12])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1

Participants

3

Reactant 1

HCID 21771543HCID 21771543, compound

Product 1

HCID 11108626HCID 11108626, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
80 °C

Procedure

N-((6-Iodobenzo[d][1,3]dioxol-5-yl)methyl)acetamide (2.4 g, 7.5 mmol) was added to methanolic hydrochloric acid solution (4 N) (60 mL). The mixture was stirred at 80° C. overnight. Solvent was removed and the residue was dissolved in water, adjusted to PH7 with 10% NaHCO3, filtered to obtain (6-iodobenzo[d][1,3]dioxol-5-yl)methanamine as a yellow solid (1.76 g, 85%). LC-MS: 278 [M+1]+. 1H-NMR (DMSO-d6): δ 1.88 (s, 2H), 3.57 (s, 2H), 6.02 (s, 2H), 7.13 (s, 1H), 7.33 (s, 1H).

Workup

  1. customSolvent was removed
  2. dissolutionthe residue was dissolved in water
  3. filtrationfiltered

Sources & evidence

ORD record
ord-75859f3919c641128339ff193cf6922a
Source dataset
uspto-grants-2016_08
Patent number
US09402832B2

Reaction notes

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