HCID 15434654, compound → HCID 9952326, compound

HRID 369487Notes

Reaction equation

HRID 369487 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([CH2:24][CH2:25][Cl:26])[C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11]C)=[O:10])=[CH:7][C:6]=1[O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>Cl>[Cl:1][CH2:2][CH2:3][N:4]([CH2:24][CH2:25][Cl:26])[C:5]1[CH:14]=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

3

Reactant 1

HCID 15434654HCID 15434654, compound

Product 1

HCID 9952326HCID 9952326, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of methyl 4-bis(2'-chloroethyl)amino-3-octoxybenzoate (1.8 g, 4.5 mmol) in concentrated HCl (37% w/w in H2O, 50 mL) was heated to refluxing under N2 for 0.5 hour. The reaction mixture was treated with ice/H2O (100 mL), extracted with chloroform (3×50 mL). The organic extract was concentrated to give a brown oil. Flash chromatographic purification (silica gel, 2% methanol in chloroform) gave the product 4-bis(2'-chloroethyl)amino-3-octoxybenzoic acid as an off-white solid (1.58 g, 88%). 1H NMR (300 MHz, CDCl3): 7.67 (dd, J=8.1, 1.5 Hz, 1H), 7.56 (d, J=1.5 Hz, 1H), 6.93 (d, J=8.4 Hz, 1H), 4.40 (d, J=6.6 Hz, 2H), 3.65 (m, 8H), 1.85 (J=7.8 Hz, 2H), 1.35 (m, 10H), 0.90 (t, J=6.6 Hz, 3H). ESMS calcd (C29H29Cl2NO3): 389.2; found: 390.2 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto refluxing under N2 for 0.5 hour
  3. extractionextracted with chloroform (3×50 mL)
  4. extractionThe organic extract
  5. concentrationwas concentrated
  6. customto give a brown oil
  7. customFlash chromatographic purification (silica gel, 2% methanol in chloroform)

Sources & evidence

ORD record
ord-1f189e32c79e4a478bebd6265f1ec2a5
Source dataset
uspto-grants-2000_10
Patent number
US06137003

Reaction notes

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