Acetic Acid Mixture with Hydrobromic Acid → HCID 71212171, compound

HRID 1752260Notes

Reaction equation

HRID 1752260 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][C:7]1[N:12]=[N:11][CH:10]=[C:9]2[O:13][CH2:14][CH2:15][CH2:16][C:8]=12.[BrH:23].C(O)(=O)C>C(O)(=O)C>[BrH:23].[O:13]1[C:9]2=[CH:10][N:11]=[N:12][C:7]([NH2:6])=[C:8]2[CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 71212232HCID 71212232, compound

Product 1

HCID 71212171HCID 71212171, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of N-(2,4-dimethoxybenzyl)-3,4-dihydro-2H-pyrano[2,3-d]pyridazin-5-amine (158, 0.524 mmol) and 30% by weight hydrobromic acid/acetic acid (0.3 mL, 0.4 g, 1.5 mmol) in acetic acid (3 mL) was stirred nearly 2 hours at 90° C. The reaction was then cooled to room temperature and the solvents were removed in vacuo. The dark red solid was washed with diethyl ether and then dried to afford the crude title compound (122 mg) in about 65% purity. MS (ESI) [m/e, (M)+]=151.7. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.22 (s, 1H), 8.11 (br s, 2H), 4.36-4.40 (m, 2H), 2.47 (t, J=6.32 Hz, 2H), 1.98-2.06 (m, 2H).

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. customthe solvents were removed in vacuo
  3. washThe dark red solid was washed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-e4a462e78d2a41669748400ff460cefb
Source dataset
uspto-grants-2015_10
Patent number
US09163003B2

Reaction notes

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