HCID 18761413, compound → HCID 18761430, compound

HRID 431715Notes

Reaction equation

HRID 431715 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][Cl:17])=[C:11]([N+:18]([O-])=O)[CH:10]=1)C1C=CC=CC=1>[Pd].C1COCC1>[NH2:18][C:11]1[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][C:12]=1[CH2:15][CH2:16][Cl:17]

Participants

4

Reactant 1

HCID 18761413HCID 18761413, compound

Product 1

HCID 18761430HCID 18761430, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Pd/C 10% (45 mg) was added to 2-(4-benzyloxy-2-nitrophenyl)ethyl chloride (132 mg, 0.453 mmol). The mixture was then suspended in freezer chilled THF (30 mL). The suspension was degassed and purged 3 times with hydrogen and reduced under atmospheric pressure at room temperature. After 3 h the solution was checked by TLC (10% MeOH/CHCl3) and the solution was filtered by suction over Celite. The filter residue was washed with more CH2Cl2, and the filtrate was concentrated under reduced pressure to give 2-(2-amino-4-hydroxyphenyl)ethyl chloride as a white solid (60.7 mg, 0.354 mmol, 78%). Mp 96-100° C.; TLC (10% MeOH/CHCl3) Rf=0.34; 1H-NMR (CDCl3 in 1 drop DMSO-d6, 500 MHz) 8.20 (br s, 1H), 6.85 (d, 8.0, 1H), 6.27 (dd, 2.5, 8.0, 1H), 6.26 (d, 2.5, 1H), 4.00 (br s, 2H), 3.66 (t, 8.5, 2H), 2.90 (t, 8.5, 2H); IR (neat) 3139, 3020, 2954, 1622, 1594, 1513, 1464, 1560, 1306, 1265, 1246, 1197, 1175, 1079, 1049, 973, 848, 793, 722, 596, 646; EI-MS m/z (relative intensity) 171 (M+, 28); isotope pattern of M+ and M++2 agrees with the presence of one chlorine atom. Accurate mass (EI-MS) for C8H10ClNO: calcd. 171.0451, obsd. 171.0444.

Workup

  1. customThe suspension was degassed
  2. custompurged 3 times with hydrogen
  3. customreduced under atmospheric pressure at room temperature
  4. filtrationthe solution was filtered by suction over Celite
  5. washThe filter residue was washed with more CH2Cl2
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c6f14f0660ee43f6a855ffd62089830b
Source dataset
uspto-grants-2003_12
Patent number
US06660742B2

Reaction notes

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