Hydrochloric Acid → HCID 69978538, compound

HRID 2302009Notes

Reaction equation

HRID 2302009 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH2:16][CH2:17][CH2:18][N:19]3C(=O)C4C(=CC=CC=4)C3=O)[CH:11]=2)[CH2:6]1.NN.Cl>C(O)(C)C>[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH2:16][CH2:17][CH2:18][NH2:19])[CH:11]=2)[CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 69979369HCID 69979369, compound

Product 1

HCID 69978538HCID 69978538, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
55 °C

Procedure

To a suspension of {6-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propoxy]-1,2,3,4-tetrahydro-naphthalen-2-yl}-acetic acid methyl ester, (17.7 g) in isopropyl alcohol (350 mL) heated at 55° C. was added hydrazine (3 mL). The mixture was heated to reflux for 1.5 h, then the reaction mixture was allowed to stand at room temperature overnight. Concentrated HCl (7.8 mL) was added, the mixture was stirred for 10 minutes, and filtered. The white solid was washed with isopropyl alcohol. The filtrate was concentrated under reduced pressure and applied to a silica gel column. Elution with 2% NH4OH/10% MeOH/CH2Cl2 afforded the product of the example as a golden oil which solidified on standing (8.0 g). NMR (300 MHz, CDCl3) δ6.95 (d, J=8.34 Hz, 1H), 6.67 (dd, J=8.30, 2.55 Hz, 1H), 6.62 (d, J=2.16 Hz, 1H), 4.01 (t, J=6.07 Hz, 2H), 3.69 (s, 3H), 2.93 (broad s, 2H), 2.86-2.77 (m, 3H), 2.46-2.36 (m, 3H), 2.26-2.18 (m, 1H), 2.12-1.98 (broad s, 2H), 1.93 (m, 3H), 1.51-1.38 (m, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 h
  3. filtrationfiltered
  4. washThe white solid was washed with isopropyl alcohol
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. washElution with 2% NH4OH/10% MeOH/CH2Cl2
  7. customafforded the product of the example as a golden oil which

Sources & evidence

ORD record
ord-f8b776adf2f54e0ba79e7c032e3f9aa4
Source dataset
uspto-grants-2002_08
Patent number
US06429214B1

Reaction notes

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