Methanimidamide, hydrochloride (1:1) → HCID 178496103, compound

HRID 631278Notes

Reaction equation

HRID 631278 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][O:15][CH3:16])=[CH:8][C:3]=1[C:4](OC)=[O:5].Cl.[CH:18](N)=[NH:19]>CCO>[OH:5][C:4]1[C:3]2[C:2](=[CH:11][CH:10]=[C:9]([O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:8]=2)[N:1]=[CH:18][N:19]=1

Participants

4

Reactant 2

HCID 10313058Methanimidamide, hydrochloride (1:1)HCID 61305437Methyl 2-amino-5-(2-methoxyethoxy)benzoate

Product 1

HCID 178496103HCID 178496103, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

To methyl 2-amino-5-(2-methoxyethoxyl)benzoate (964 mg, 4.2 mmol) in absolute EtOH (25 mL) was added formamidine hydrochloride (1.4 g, 17.2 mmol) and the mixture heated in a sealed tube at 130° C. overnight. The mixture was cooled to room temperatureand filtered to give 4-hydroxy-6-(2-methoxyethoxy)quinazoline (871 mg, 4.0 mmol, 95%). 1H NMR (300 MHz, DMSO-d6) δ 8.42 (br s, 1H), 7.99 (s, 1H), 7.61 (d, 1H), 7.50 (d, 1H), 7.43 (dd, 1H), 4.21 (dd, 2H), 3.70 (dd, 2H), 3.32 (s, 3H); LC-MS (ESI) m/z 221 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to room temperatureand
  2. filtrationfiltered

Sources & evidence

ORD record
ord-ad41f5033e2e440189e5ff777cfa8d08
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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