Hydrochloric Acid → HCID 70874054, compound

HRID 2208840Notes

Reaction equation

HRID 2208840 reaction equation
[Br:1][C:2]1[C:11]([N:12]([CH2:19][CH3:20])[CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:10][C:9]([Cl:21])=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+].Cl>O1CCCC1>[Br:1][C:2]1[C:11]([N:12]([CH2:19][CH3:20])[CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:10][C:9]([Cl:21])=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70873606HCID 70873606, compound

Product 1

HCID 70874054HCID 70874054, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 2-bromo-5-chloro-3-[ethyl(oxan-4-yl)amino]benzoate (122 mg, 0.32 mmol) in tetrahydrofuran (3 ml) was added 4M NaOH (3.2 ml). The reaction mixture was stirred at 50° C. for 20 hours. The reaction mixture was acidified to pH 2-3 with 6M HCl and extracted with DCM (3×100 ml). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to give 109 mg (93%, 83% corrected yields) of 2-bromo-5-chloro-3-[ethyl(oxan-4-yl)amino]benzoic acid as a pale yellow foam. LC-MS 89%, m/z=361.9/364.2/365.8, 1H NMR (500 MHz, Chloroform-d) δ 7.50 (d, J=2.4 Hz, 1H), 7.23 (d, J=2.4 Hz, 1H), 4.00 (d, J=11.5 Hz, 2H), 3.49-3.27 (m, 2H), 3.21 (t, J=7.4 Hz, 1H), 3.14 (q, J=7.0 Hz, 2H), 1.78 (dd, J=7.4, 3.4 Hz, 4H), 0.93 (t, J=7.0 Hz, 3H).

Workup

  1. extractionextracted with DCM (3×100 ml)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f3eeb82e4360409b87d25e6f67c7aeaf
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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