Methanol → HCID 67429396, compound

HRID 1921651Notes

Reaction equation

HRID 1921651 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][C:12]([OH:14])=[O:13])=[CH:8][CH:9]=2)[CH:4]=[N:3][CH:2]=1.S(Cl)(Cl)=O.[CH3:19]O>>[CH3:19][O:13][C:12](=[O:14])[CH2:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][N:3]=[CH:4]2

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 57654546HCID 57654546, compound

Product 1

HCID 67429396HCID 67429396, compound

Procedure

A solution of quinazolin-6-yl-acetic acid (0.025 g, 0.133 mmol), thionyl chloride (0.1 mL) and methanol (2 mL) was heated to 60° C. for 6 hours. The reaction was cooled to room temperature and evaporated several times with dichloromethane to give quinazolin-6-yl-acetic acid methyl ester. This was dissolved in a solution of methanol (2 mL) and hydrazine (0.061 mL) and stirred at room temperature for several hours. The reaction was evaporated in vacuo to give quinazolin-6-yl-acetic acid hydrazide. 1H NMR (400 MHz, DMSO-d6) δ 9.56 (s, 1H), 9.33 (bs, 1H), 9.26 (s, 1H), 7.96 (m, 3H), 4.25 (bs, 2H), 3.84 (s, 2H).

Workup

  1. customevaporated several times with dichloromethane

Sources & evidence

ORD record
ord-df6a6b4b49c649d693673509af7640f4
Source dataset
uspto-grants-2012_05
Patent number
US08173654B2

Reaction notes

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