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Methylamine → Benzyl 5-[3-(aminooxy)propoxy]-3-chlorobenzoate

HRID 1698861
Notes
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Reaction equation

HRID 1698861 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:18]=[C:19]([Cl:33])[CH:20]=[C:21]([CH:32]=1)[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23].CN>O1CCCC1>[NH2:3][O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:18]=[C:19]([Cl:33])[CH:20]=[C:21]([CH:32]=1)[C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6329MethylamineHCID 18322169Benzyl 5-[3-(1,3-dioxoisoindolin-2-yloxy)propoxy]-3-chlorobenzoate

Product 1

HCID 18322200Benzyl 5-[3-(aminooxy)propoxy]-3-chlorobenzoateYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of phthalimide 27 (1.00 g, 2.15 mmol) in tetrahydrofuran (20 mL) was added a 40% aqueous solution of methylamine (0.148 mL, 1.72 mmol). After stirring 25 minutes at 0° C., the reaction was evaporated in vacuo, the residue partitioned between methylene chloride and water, and the organic layer dried over Na2SO4 and filtered. The evaporated filtrate was then purified by chromatography on silica gel (40% ethyl acetate in hexanes) giving product 28 (0.576 g, 80%). 1H NMR (300 MHz, CDCl3) δ 7.62 (t, 1H, J=1.6 Hz), 7.48 (dd, 1H, J=2.4 Hz, 1.4 Hz), 7.45-7.32 (m, 5H), 7.08 (t, 1H, J=2.1 Hz), 5.35 (s, 2H), 4.07 (t, 2H, J=6.3 Hz), 3.82 (t, 2H, J=6.3 Hz), 2.07 (pentet, 2H, J=6.3 Hz).

Workup

  1. customthe reaction was evaporated in vacuo
  2. customthe residue partitioned between methylene chloride and water
  3. dry with materialthe organic layer dried over Na2SO4
  4. filtrationfiltered
  5. customThe evaporated filtrate was then purified by chromatography on silica gel (40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-55aa790831d74389b750dd3982749da4
Source dataset
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06344466B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes