Hydrochloric Acid → HCID 15703641, compound

HRID 2351278Notes

Reaction equation

HRID 2351278 reaction equation
[CH2:1]([O:3][C:4]1[O:9][C:8](=[O:10])[C:7]2[C:11]([CH3:15])=[CH:12][CH:13]=[CH:14][C:6]=2[N:5]=1)[CH3:2].Cl.[O:17]1CCCC1>>[CH2:1]([O:3][C:4]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:7]=1[C:8]([OH:17])=[O:10])=[O:9])[CH3:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 504661HCID 504661, compound

Product 1

HCID 15703641HCID 15703641, compoundYield 74%

Procedure

2-Ethoxy-5-methyl-4H-3,1-benzoxazin-4-one (20 g., 97.56 mmol) of Preparation III herein, and 4N HCl (10 ml), were stirred in tetrahydrofuran (THF, 200 ml) at room temperature for 15 minutes. The reaction mixture was evaporated to dryness under reduced pressure. The residue was dissolved in ethyl acetate (250 ml), washed with water (3×150 ml), and evaporated to give a pale yellow solid. Recrystallization from ethyl acetate/ pet. ether afforded 2-ethoxycarbonylamino-6-methylbenzoic acid (16.18 g, 74%) as colorless crystals; m.p. 123.5°-125° C.; analysis for C11H13NO4 : C, 59.19; H, 5.87; N, 6.27. Found: C, 59.32; H, 5.95; N, 6.25.

Workup

  1. customThe reaction mixture was evaporated to dryness under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (250 ml)
  3. washwashed with water (3×150 ml)
  4. customevaporated
  5. customto give a pale yellow solid
  6. customRecrystallization from ethyl acetate/ pet. ether

Sources & evidence

ORD record
ord-535920f735dd4c07bb3e74f3fd9b6249
Source dataset
uspto-grants-1989_10
Patent number
US04873232

Reaction notes

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