Methanimidamide, hydrochloride (1:1) → HCID 178486871, compound

HRID 1917684Notes

Reaction equation

HRID 1917684 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH2:15][CH2:16][Cl:17])=[CH:8][C:3]=1[C:4](OC)=[O:5].Cl.[CH:19](N)=[NH:20]>C(O)C>[Cl:17][CH2:16][CH2:15][O:14][C:9]1[CH:8]=[C:3]2[C:2](=[CH:11][C:10]=1[O:12][CH3:13])[N:1]=[CH:19][N:20]=[C:4]2[OH:5]

Participants

4

Reactant 2

HCID 10313058Methanimidamide, hydrochloride (1:1)HCID 66876719HCID 66876719, compound

Product 1

HCID 178486871HCID 178486871, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of methyl 2-amino-5-(2-chloroethoxy)-4-methoxybenzoate (3.61 g, 13.9 mmol) in ethanol was added formamidine hydrochloride and the mixture heated in a sealed tube at 130° C. overnight. The reaction was cooled to room temperature and filtered to give 6-(2-chloroethoxy)-4-hydroxy-7-methoxyquinazoline (3.05 g, 12.0 mmol, 86%). 1H NMR (300 MHz, DMSO-d6) δ 12.09 (br s, 1H), 8.00 (s, 1H), 7.47 (s, 1H), 7.16 (s, 1H), 4.36 (t, 2H), 4.00 (t, 2H), 3.92 (s, 3H); LC-MS (ESI) m/z 255 (M+H)+.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered

Sources & evidence

ORD record
ord-a4756fb657c24671b4520ed716204182
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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