Ethyl orthoformate → HCID 60757901, compound

HRID 2173425Notes

Reaction equation

HRID 2173425 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH:12](OCC)(OCC)OCC.[N-:22]=[N+:23]=[N-:24].[Na+]>C(O)(=O)C>[N:1]1([C:2]2[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=2)[CH:12]=[N:24][N:23]=[N:22]1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 571807(3-Aminophenyl)acetic acid

Product 1

HCID 60757901HCID 60757901, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Aminophenylacetic acid (1.0 g, 6.62 mmol) was stirred in acetic acid (15 ml) and added triethyl orthoformate (2.203 ml, 13.23 mmol) followed by sodium azide (0.774 g, 11.91 mmol) then heated to reflux for 3 hrs. The reaction was concentrated and added water then extracted with ethyl acetate and tetrahydrofuran (2×). The organic layers were combined and washed with brine (1×), then dried over Na2SO4 and evaporated to dryness. The residue was triturated with ether, filtered and dried to yield [3-(1H-tetrazol-1yl)phenyl]acetic acid. LC-MS (IE, m/z): 205 [M+1]+; 1H-NMR (500 MHz, DMSO) δ ppm 12.45 (b, 1H), 10.1 (s, 1H), 7.84 (s, 1H), 7.79 (dd, J=8 Hz, 1.4 Hz, 1H), 7.59 (t, J=7.9 Hz, 1H), 3.73 (s, 2H);

Workup

  1. temperaturethen heated
  2. temperatureto reflux for 3 hrs
  3. concentrationThe reaction was concentrated
  4. additionadded water
  5. extractionthen extracted with ethyl acetate and tetrahydrofuran (2×)
  6. washwashed with brine (1×)
  7. dry with materialdried over Na2SO4
  8. customevaporated to dryness
  9. customThe residue was triturated with ether
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-f78f5f2e65194dba8ebdadca2f4c651c
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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