Dimethylformamide dimethyl acetal → HCID 178497026, compound

HRID 82471Notes

Reaction equation

HRID 82471 reaction equation
Br.[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([Br:13])=[CH:5][C:4]=1[C:14]([O:16][CH3:17])=[O:15].CO[CH:20](OC)[N:21]([CH3:23])[CH3:22]>>[Br:13][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3](/[N:2]=[CH:20]/[N:21]([CH3:23])[CH3:22])=[C:4]([C:14]([O:16][CH3:17])=[O:15])[CH:5]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetal2×HCID 66979039Methyl 1-amino-4-bromo-2-naphthoate hydrobromide

Product 1

HCID 178497026HCID 178497026, compound

Conditions

Temperature
100 °C

Procedure

A solution of methyl 1-amino-4-bromo-2-naphthoate hydrobromide (see Example 1, 3.20 g, 8.86 mmol) in N,N-dimethylformamide dimethylacetal (3.56 mL, 26.6 mmol) was heated at 100° C. for 2 h. Additional N,N-dimethylformamide dimethylacetal (1.19 mL, 8.9 mmol) was added and the solution was heated at 100° C. for an additional 3 h. The reaction was cooled to rt, concentrated, and dried to provide crude methyl 4-bromo-1-{[(1E)-(dimethylamino)methylene]amino}-2-naphthoate that gave a mass ion (ES+) of 337.1 (81Br) for [M+H]+.

Workup

  1. temperatureThe reaction was cooled to rt
  2. concentrationconcentrated
  3. customdried

Sources & evidence

ORD record
ord-de98816b9612488b9de7ad4fdbbeec56
Source dataset
uspto-grants-2014_09
Patent number
US08846702B2

Reaction notes

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