Ammonia → HCID 4532577, compound

HRID 1669127Notes

Reaction equation

HRID 1669127 reaction equation
[N+:1]([C:4]1[C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[CH:7]=[CH:6][C:5]=1[NH:14]C(=O)C)([O-:3])=[O:2].N>Cl.O>[N+:1]([C:4]1[C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[CH:7]=[CH:6][C:5]=1[NH2:14])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 57447687HCID 57447687, compound

Product 1

HCID 4532577HCID 4532577, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of acetamide 168 (835 mg, 4.4 mmol) in 6 M HCl (50 mL) was stirred at 100° C. for 16 h. The suspension was cooled to 20° C., diluted with water (50 mL) and the pH adjusted to 8 with dilute aqueous NH3 solution. The mixture was extracted with DCM (3×50 mL), the combined organic fraction dried and the solvent evaporated. The residue was purified by chromatography, eluting with 20% EtOAc/pet. ether, to give amine 169 (755 mg, 56%) as an orange solid: mp (EtOAc/pet. ether) 76-78° C.; 1H NMR δ 6.98 (d, J=8.4 Hz, 1H, H-4), 6.58 (d, J=8.4 Hz, 1H, H-3), 4.73 (br s, 2H, NH2), 2.76-2.81 (m, 2H, CH2), 2.65-2.69 (m, 2H, CH2), 1.69-1.78 (m, 2H, CH2). Anal. calcd for C10H12N2O2: C, 62.5; H, 6.3; N, 14.6. Found: C, 62.8; H, 6.1; N, 14.6%.

Workup

  1. temperatureThe suspension was cooled to 20° C.
  2. extractionThe mixture was extracted with DCM (3×50 mL)
  3. customthe combined organic fraction dried
  4. customthe solvent evaporated
  5. customThe residue was purified by chromatography
  6. washeluting with 20% EtOAc/pet. ether

Sources & evidence

ORD record
ord-b67fb266fbfd4a67b671da3f898747d0
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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