Cyclopropanecarboxaldehyde → HCID 178517405, compound

HRID 1403094Notes

Reaction equation

[CH:1]1([CH:4]=O)[CH2:3][CH2:2]1.[NH2:6][C:7]1[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([NH2:11])=[O:10]>O.O.O.O.O.O.O.[Fe](Cl)(Cl)Cl>[Cl:16][C:15]1[CH:14]=[CH:13][CH:12]=[C:8]2[C:7]=1[NH:6][C:4]([CH:1]1[CH2:2][CH2:3]1)=[N:11][C:9]2=[O:10]

Participants

Conditions

Temperature: 100 °C

Procedure

EDCI hydrochloride (22.0 g) and 1-hydroxybenzotriazole (11.4 g) were added to a solution of 2-amino-3-chlorobenzoic acid (12.8 g) in DMF (100 mL), and subsequently ammonia water (22.0 ml) was added thereto. The reaction solution was stirred at room temperature for 3 hours. Water was added to the reaction solution, and the deposit was filtrated and dried under reduced pressure to obtain 2-amino-3-chlorobenzamide (9.7 g). Iron(III) chloride hexahydrate (6.3 g) and cyclopropanecarbaldehyde (1.3 ml) were added to a suspension of the obtained 2-amino-3-chlorobenzamide (2.0 g) in water (30 ml), and the mixture was stirred overnight at 100° C. After cooling, water was added to the reaction solution, and the deposit was filtrated and dried under reduced pressure to obtain 8-chloro-2-cyclopropylquinazolin-4(1H)-one (2.0 g). Compound (115) was obtained as a yellow solid (yield based on 6 steps: 18%) according to Example 114(2) using the obtained 8-chloro-2-cyclopropylquinazolin-4(1H)-one instead of compound (114a).

Workup

temperatureAfter cooling
filtrationthe deposit was filtrated
customdried under reduced pressure

Sources & evidence

ORD record: ord-43ae76b113cb45d8a1d4c638c46d0973
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912181B2

Reaction notes

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