Hydrochloric Acid → 5-(Benzyloxy)-2-methoxybenzamide

HRID 922400Notes

Reaction equation

HRID 922400 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:18][CH3:19])=[C:13]([CH:17]=1)[C:14](O)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[NH4+:26].[OH-].Cl>C(Cl)Cl.C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:18][CH3:19])=[C:13]([CH:17]=1)[C:14]([NH2:26])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 132820475-(Benzyloxy)-2-methoxybenzoic Acid

Product 1

HCID 215044235-(Benzyloxy)-2-methoxybenzamideYield 63%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 5-(benzyloxy)-2-methoxybenzoic acid (8, 1.16 g. 4.5 mmol) in CH2Cl2 (25 mL) at room temperature was added oxalyl chloride (1.5 mL, 17.9 mmol). The reaction mixture was stirred at room temperature for 2 h. It was concentrated to dryness to provide the crude acid chloride as a brown-yellow waxy solid. The crude acid chloride was dissolved in THF (10 mL) and was added dropwise to a stirred mixture of concentrated NH4OH (20 mL) and THF (10 mL) at 0° C. The reaction mixture was warmed to room temperature and stirred for 1 h and was adjusted to pH 8 with 2 N HCl. The precipitate was collected, washed with water, and dried in vacuo to afford the title compound (0.73 g, 63%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 7.88 (d, J=3.3 Hz, 1H), 7.82 (br s, 1H), 7.47-7.43 (m, 2H), 7.40-7.37 (m, 2H), 7.33-7.30 (m, 1H), 7.10 (dd, J=9.0, 3.3 Hz, 1H), 6.94 (d, J=9.0 Hz, 1H), 5.75 (br s, 1H), 5.08 (s, 2H), 3.94 (s, 3H); ESI MS m/z 258 [M+H]+.

Workup

  1. concentrationIt was concentrated to dryness
  2. customto provide the crude acid chloride as a brown-yellow waxy solid
  3. temperatureThe reaction mixture was warmed to room temperature
  4. stirringstirred for 1 h
  5. customThe precipitate was collected
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-e56e933fe70e44d98bde925c39c74a27
Source dataset
uspto-grants-2016_03
Patent number
US09278940B2

Reaction notes

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