Acetic Acid → 5-Hydroxybenzo[d]oxazole-4-carbaldehyde

HRID 579472Notes

Reaction equation

HRID 579472 reaction equation
ClC1C=C[C:9]2[C:8]([CH:12]=[O:13])=[C:7]([OH:14])[CH:6]=[CH:5][C:4]=2N=1.C1N2CN3[CH2:24][N:18](C2)CN1C3.CC(O)=[O:27]>>[OH:14][C:7]1[C:8]([CH:12]=[O:13])=[C:9]2[N:18]=[CH:24][O:27][C:4]2=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 4101HexamethylenetetramineHCID 866834282-Chloro-6-hydroxyquinoline-5-carbaldehyde

Product 1

HCID 874070885-Hydroxybenzo[d]oxazole-4-carbaldehydeYield 25%

Conditions

Temperature
90 °C

Procedure

A mixture of compound 3 (350 mg, 1.05 mmol) and HMTA (560 mg, 4 mmol) in AcOH (35 mL) was heated to 90° C. under N2 for 1.5 h. The reaction was monitored by LCMS. After cooled to RT, the solvent was removed under vacuum. The residue was purified by prep-HPLC to give 5-hydroxybenzo[d]oxazole-4-carbaldehyde (152 mg, 25% yield). 1HNMR (DMSO, 400 MHz): δ 10.99 (s, 1H, OH), 10.53 (s, 1H, CHO), 8.86 (s, 1H, ArH), 8.00 (d, 1H, J=9.2 Hz, ArH), 7.05 (d, 1H, J=8.8 Hz, ArH). MS [ESI, MH+]: 164.1.

Workup

  1. temperatureAfter cooled to RT
  2. customthe solvent was removed under vacuum
  3. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-8b722fff7a2b4a7f81bc31a0889b6d8f
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

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